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Barrelene Synthesis Essay

DOI: 10.1039/A803481H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 2, 1998, 1893-1900

Laticyclic conjugated double bonds within the framework of oligocondensed bicyclo[2.2.2]octenes

(Note: The full text of this document is currently only available in the PDF Version )


The all-syn oligocondensed bicyclo[2.2.2]octenes 3, 5, 20 and 29 with two to five etheno bridges show interaction of their π-orbitals by σ-overlap. This laticyclic conjugation reveals itself in the PE and UV spectra of the series as well as in the site selectivity of the Diels–Alder reaction with inverse electron demand found for the dehydro derivatives 11 and 26. As shown in the crystal structures of 3, 5 and 20, the etheno bridges are positioned face to face at a distance which is smaller than the sum of their van der Waals radii.


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Publications

 

  1. "Synthetic Peroxides as Potent Antimalarials. News and Views"
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  1. "Synthetic peroxides as antimalarials"
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  1. "Photochemical Study of [33](1,3,5)Cyclophane and Emission Spectral Properties of [3n]Cyclophanes (n = 2-6)"
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  1. "A Concise Synthesis of Siphonodictidine"
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  1. "PREFACE [Hot Topic: Heterocyclic Chemistry (Guest Editor: Charles W. Jefford)]"
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  1. "A kinetic and mechanistic study on the thermal decomposition reactions of cis- and trans-fused 1,2,4-trioxanes"
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  1. "Kinetics and mechanism of thermolysis of fluorine-substituted 1,2,4-trioxanes in n-hexane solution"
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  1. "Solvent and Substituent Effects on the Kinetics of Thermolysis of cis-Fused 1,2,4-Trioxanes"
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    J. Nat. Prod.2001, 64, 696-700
  1. "Kinetics and mechanism of thermolysis of fluorine substituted 1,2,4-trioxanes in methanol solution"
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  1. "3-Bromobarekoxide, an unusual diterpene from Laurencia luzonensis"
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  1. "Pyrroles as Building Blocks for the Enantioselective Synthesis of Indolizidines"
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  1. "Preface"
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    J. Chem. Inform. Comput. Sci.2000, 40, 354-357
  1. "Stereoselective Oxidative Dimerization of (1R)-Camphor. A Short Synthesis of exo,exo′-3,3′-Biisoborneol"
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    J. Org. Chem.1999, 64, 5312-5314
  1. "The Efficient Synthesis of 1,2-Dioxetanes from Indene and 1,2-Dihydronaphthalene"
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  1. "The Structure and Antimalarial Activity of Some cis-Fused Bicyclic 1,2,4-Trioxane Derivatives"
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  1. "Highly Diastereoselective Conjugate Addition of Lithiated γ-Crotonolactone (But-2-en-4-olide) to Cyclic Enones To Give Syn-Adducts: Application to a Brefeldin Synthesis"
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    J. Org. Chem.1998, 63, 5294
  1. "Synthesis of Polycyclic 1,2-Dioxanes from Endoperoxides"
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  1. "The Photo-Oxygenation of Dihydropyrans. Formation of 1,2-Dioxetanes and 1,2,4-Trioxanes"
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  1. "The Diastereoselective Formation of 1,2,4-Trioxanes and 1,3-Dioxolanes by the reaction of endoperoxides with chiral cyclohexanones"
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  1. "Peroxidic antimalarials"
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    in Advances in Drug Research; Advances in Drug Research, 1997; Vol. 29; p. 271-325
  1. "Synthesis of Enantiometrically Pure β-Amino Acids Starting from L- and D-Aspartic Acids"
    Jefford, C. W.; McNulty, J.
    in Enantioselective Synthesis of β-Amino Acids; Juaristi, and E. (Ed.)Wiley, 1997; p. 83-104
  1. "A QSAR Study of the Antimalarial Activity of Some Synthetic 1,2,4-Trioxanes"
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    J. Chem. Inf. Comput. Sci.1997, 37, 124-130
  1. "cis-Fused Dihydrofurano-1,2,4-trioxanes"
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  1. "The Enantioselective Synthesis of β-Amino Acids, their α-hydroxy derivatives, and the N-terminal components of bestatin and microginin"
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  1. "The Deoxygenation and Isomerization of Artemisinin and Artemether and Their Relevance to Antimalarial Action"
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    Helv. Chim. Acta1996, 79, 1475-1487
  1. "The synthesis of chiral 1-(1H-pyrrole) derivatives"
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    Tetrahedron: Asymmetry1996, 7, 1069-1076
  1. "Heterocyclic templates for assembling α-hydroxy-β-amino acids, sphingosines and indolizidines"
    Jefford, C. W.
    Pure Appl. Chem.1996, 68, 799-804
  1. "New Cytotoxic Macrolides from the Sponge Fasciospongia rimosa"
    Tanaka, J.-i.; Higa, T.; Bernardinelli, G.; Jefford, C. W.
    Chem. Lett.1996, 25, 255-256
  1. "Second-generation antimalarial endoperoxides"
    Meshnick, S. R.; Jefford, C. W.; Posner, G. H.; Avery, M. A.; Peters, W.
    Parasitol. Today1996, 12, 79-82
  1. "Structures and absolute configurations of the marine toxins, latrunculin A and laulimalide"
    Jefford, C. W.; Bernardinelli, G.; Tanaka, J.-i.; Higa, T.
    Tetrahedron Lett.1996, 37, 159-162
  1. "Six-membered Rings with 1,2,4-Oxygen or Sulfur Atoms"
    Jefford, C. W.
    in Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, and E. F. (Eds.)Elsevier, 1996; Volume 6; p. 861-899
  1. "Short, Enantiospecific Syntheses of Indolizidines 209B and 209D, and Piclavine A from Diethyl-L-Glutamate"
    Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R.
    Helv. Chim. Acta1995, 78, 1511-1524
  1. "Amplified Asymmetric Dihydroxylation of a Racemic Cyclopentene"
    Jefford, C. W.; Timári, G.
    J. Chem. Soc., Chem. Commun.1995, 1501-1502
  1. "Comparative modelling studies on 3,6-substituted 1,2,4-trioxan-5-ones"
    Jefford, C. W.; Bernardinelli, G.; Josso, M. C.; Morgantini, P.-Y.; Weber, J.
    J. Mol. Struct. Theochem1995, 337, 31-37
  1. "Synthesis, Structure, and Antimalarial Activity of Some Enantiomerically Pure, cis-fused cyclopenteno-1,2,4-trioxanes"
    Jefford, C. W.; Kohmoto, S.; Jaggi, D.; Timári, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gérard, D.; Burger, U.; Kamalaprija, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C. J.; Feck, S. L.; Robinson, B. L.; Peters, W.
    Helv. Chim. Acta1995, 78, 647-662
  1. "The Decomposition of cis-Fused Cyclopenteno-1,2,4-Trioxanes induced by Ferrous Salts and some oxophilic reagents"
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    Helv. Chim. Acta1995, 78, 452-458
  1. "A Concise Enantioselective Synthesis of N-Morpholinosphingosines from D-Aspartic Acid"
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    J. Chem. Soc., Chem. Commun.1995, 123-124
  1. "A Practical Synthesis of (2S, 3R)-3-Amino-2-methylpentanoic Acid from L-Aspartic Acid"
    Jefford, C. W.; McNulty, J.
    Helv. Chim. Acta1994, 77, 2142-2146
  1. "Thermolysis and Chemiluminescence of Monocyclic 1,2,4-Trioxan-5-ones"
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    Helv. Chim. Acta1994, 77, 1851-1860
  1. "Concise enantiospecific syntheses of α-hydroxy-β-amino acids and indolizidines of natural origin"
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  1. "The osmium-catalyzed asymmetric dihydroxylation of cis-fused cyclopenteno-1,2,4-trioxanes"
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    Tetrahedron Lett.1994, 35, 6275-6278
  1. "A concise synthesis of two pyrroles of marine origin"
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  1. "Helioxenicins A-C: Diterpenes from the blue coral Heliopora coerulea"
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  1. "The enantiospecific synthesis of (-)-monomorine from L-glutamic ester"
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  1. "An enantiospecific entry to indolizidines by intramolecular acylation of N-pyrrole esters"
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  1. "A Concise Synthesis of (E)- and (Z)-Neomanoalides"
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  1. "Computational studies of the structures and properties of potential antimalarial compounds based on the 1,2,4-trioxane ring structure. I. Artemisinin-like molecules"
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  1. "Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin"
    Jefford, C. W.; Velarde, J. A.; Bernardinelli, G.; Bray, D. H.; Warhurst, D. C.; Milhous, W. K.
    Helv. Chim. Acta1993, 76, 2775-2788
  1. "A concise diastereospecific synthesis of 3-amino-2-hydroxy acids"
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    Tetrahedron Lett.1993, 34, 7557-7560
  1. "Short, novel syntheses of lactones and furans of marine origin"
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    Gazz. Chim. Ital.1993, 123, 317-320
  1. "Enantiospecific syntheses of indolizidines 167B and 209D"
    Jefford, C. W.; Wang, J. B.
    Tetrahedron Lett.1993, 34, 3119-3122
  1. "On the Decomposition of 1,2,4-Trioxan-5-ones"
    Jefford, C. W.; Vicente, M. G. H.
    Heterocycles1993, 35, 725-729
  1. "Bioactive norsesterterpene 1,2-dioxanes from a Thai sponge, Mycale sp"
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    J. Org. Chem.1993, 58, 2999-3002
  1. "An enantiospecific synthesis of solenopsin A"
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    Tetrahedron Lett.1993, 34, 2911-2914
  1. "An enantiospecific synthesis of β-amino acids"
    Jefford, C. W.; Wang, J.
    Tetrahedron Lett.1993, 34, 1111-1114
  1. "The photo-oxygenation of olefins and the role of zwitterionic peroxides"
    Jefford, C. W.
    Chem. Soc. Rev.1993, 22, 59-66
  1. "Crystal structure of 1',2',3',4'-tetrahydronaphthaleno[1',2'e]-3,3-dimethyl-1,2,4-trioxine, C13H16O3"
    Bernardinelli, G.; Jefford, C. W.; Hatsui, T.; Deheza, M. F.
    Z. Kristallogr.1993, 203, 126-128
  1. "A selective, heterogeneous oxidation using a mixture of potassium permanganate and cupric sulfate: (3aS,7aR)-hexahydro-(3S,6R)-dimethyl-2(3H)-benzofuranone"
    Jefford, C. W.; Li, Y.; Wang, Y.
    Org. Synth.1993, 71, 207-210
  1. "The chemotherapy of rodent malaria. L. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 3: Observations on 'Fenozan-50F', a difluorinated 3,3'-spirocyclopentane 1,2,4-trioxane"
    Peters, W.; Robinson, B. L.; Tovey, G.; Rossier, J.-C.; Jefford, C. W.
    Ann. Trop. Med. Parasitol.1993, 87, 111-123
  1. "The chemotherapy of rodent malaria. XLIX. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 2: Structure-activity studies on cis-fused cyclopenteno-1,2,4-trioxanes (fenozans) against drug-sensitive and drug-resistant lines of Plasmodium berghei and P. yoelii ssp. NS in vivo"
    Peters, W.; Robinson, B. L.; Rossier, J. C.; Misra, D.; Jefford, C. W.
    Ann. Trop. Med. Parasitol.1993, 87, 9-16
  1. "The chemotherapy of rodent malaria. XLVIII. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 1: Studies leading to the development of novel cis-fused cyclopenteno derivatives"
    Peters, W.; Robinson, B. L.; Rossier, J. C.; Jefford, C. W.
    Ann. Trop. Med. Parasitol.1993, 87, 1-7
  1. "Cyclopenteno-1,2,4-trioxanes as effective antimalarial surrogates of artemisinin"
    Jefford, C. W.; Misra, D.; Rossier, J. C.; Kamalaprija, P.; Burger, U.; Mareda, J.; Bernardinelli, G.; Peters, W.; Robinson, B. L.; Milhous, W. K.; Zhang, F.; Gosser Jr., D. K.; Meshnick, S. R.
    in Perspectives in medicinal chemistry; Testa, and B. (Ed.)Verlag Helvetica chimica acta: Basel, 1993; p. 459-472
  1. "Synthesis of 1,2-dioxanes from an endoperoxide"
    Jefford, C. W.; Jin, S.-j.; Kamalaprija, P.; Burger, U.
    Tetrahedron Lett.1992, 33, 7129-7132
  1. "Miyakolide: a bryostatin-like macrolide from a sponge, Polyfibrospongia sp"
    Higa, T.; Tanaka, J.; Komesu, M.; Garcia Gravalos, D.; Fernandez Puentes, J. L.; Bernardinelli, G.; Jefford, C. W.
    J. Am. Chem. Soc.1992, 114, 7587-7588
  1. "Photooxygenation of indene and 1,2-dihydronaphthalene: formation of 1,2-dioxetanes and 1,2,4-trioxanes"
    Jefford, C. W.; Hatsui, T.; Deheza, M. F.; Bernardinelli, G.
    CHIMIA1992, 46, 114-118
  1. "The alkylation of silyl enol ethers with SN1-unreactive iodides in the presence of silver trifluoroacetate"
    Jefford, C. W.; Sledeski, A. W.; Lelandais, P.; Boukouvalas, J.
    Tetrahedron Lett.1992, 33, 1855-1858
  1. "Two New Diterpene Isocyanides from a Sponge of the Family Adocidae"
    Sharma, H. A.; Tanaka, J.-i.; Higa, T.; Lithgow, A.; Bernardinelli, G.; Jefford, C. W.
    Tetrahedron Lett.1992, 33, 1593-1596
  1. "Torquoselectivity in the electrocyclic conversion of benzocyclobutenes to o-xylylenes"
    Jefford, C. W.; Bernardinelli, G.; Wang, Y.; Spellmeyer, D. C.; Buda, A.; Houk, K. N.
    J. Am. Chem. Soc.1992, 114, 1157-1165
  1. "Non-heme dioxygenases: a unified mechanistic interpretation of their mode of action"
    Jefford, C. W.
    Adv. Detailed React. Mech.1992, 2, 149-187
  1. "Reactions of an endoperoxide with chiral ketones. Diastereoselective formation of 1,2,4-trioxanes and 1,3-dioxolanes"
    Jefford, C. W.; Jin, S.-j.; Bernardinelli, G.
    Tetrahedron Lett.1991, 32, 7243-7246
  1. "The thermal decomposition of some 1,2,4-trioxanes"
    Jefford, C. W.; Jaber, A.; Boukouvalas, J.; Tissot, P.
    Tetrahedron Lett.1991, 188, 337-342
  1. "The Synthesis of 1,2,4-Trioxan-5-ones"
    Jefford, C. W.; Currie, J.; Richardson, G. D.; Rossier, J.-C.
    Helv. Chim. Acta1991, 74, 1239-1246
  1. "Short, enantiogenic syntheses of (-)-indolizidine 167B and (+)-monomorine"
    Jefford, C. W.; Tang, Q.; Zaslona, A.
    J. Am. Chem. Soc.1991, 113, 3513-3518
  1. "The Synthesis of Boronolide"
    Jefford, C. W.; Moulin, M.-C.
    Helv. Chim. Acta1991, 74, 336-342
  1. "1,2,4-Trioxan-5-ones, a new class of endoperoxides: structures of three representative derivatives"
    Bernardinelli, G.; Jefford, C. W.; Richardson, G. D.; Rossier, J. C.
    Acta Crystallogr., Sect. C: Cryst. Struct. Commun.1991, C47, 388-392
  1. "Assignment of the configuration of disubstituted 1,3-dienes by nuclear Overhauser effect measurements"
    Jefford, C. W.; Wang, Y.; Houk, K. N.
    J. Org. Chem.1991, 56, 856-858
  1. "1,2,4-Trioxanes, the chemistry of a new class of saturated heterocycles"
    Jefford, C. W.
    Stud. Surf. Sci. Catal.1991, 66, 555-564
  1. "trans-3,6-Dinonyl-1,2,4,5-tetroxane"
    Bernardinelli, G.; Jefford, C. W.; Jaber, A.; Boukouvalas, J.
    Acta Crystallogr., Sect. C: Cryst. Struct. Commun.1990, C46, 2476-2478
  1. "A Practical, Versatile Approach to Marine Furanosesquiterpenes. Synthesis of Siphonodictidine and Pleraplysillin-2"
    Jefford, C. W.; Huang, P.-Z.; Rossier, J.-C.; Sledeski, A. W.; Boukouvalas, J.
    Synlett1990, 745-746
  1. "Detection of carbonyl oxide from singlet p-nitrophenylchlorocarbene and oxygen"
    Liu, M. T. H.; Bonneau, R.; Jefford, C. W.
    J. Chem. Soc., Chem. Commun.1990, 1482-1483
  1. "Structure of synthetic bromobeckerelide. A case of diastereomeric selection in the solid state"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Bernardinelli, G.
    Acta Crystallogr., Sect. C: Cryst. Struct. Commun.1990, 46, 1879-1881
  1. "A short route to furanosesquiterpenes using a new siloxyfuran building block. The synthesis of freelingnite and dehydrolasiosperman"
    Jefford, C. W.; Sledeski, A. W.; Rossier, J.-C.; Boukouvalas, J.
    Tetrahedron Lett.1990, 31, 5741-5744
  1. "The Reaction of Singlet Oxygen with Adamantylideneadamantane Mediated by Rose Bengal"
    Jefford, C. W.; Estrada, M. J.; Barchietto, G.; Berclaz, T.; Geoffroy, M.
    Helv. Chim. Acta1990, 73, 1653-1658
  1. "A New Method for the Synthesis of gem-Dihydroperoxides"
    Jefford, C. W.; Li, Y.; Jaber, A.; Boukouvalas, J.
    Synth. Commun.1990, 20, 2589-2596
  1. "Regioselective 2-acylation of N-substituted pyrroles by intramolecular delivery"
    Jefford, C. W.; Tang, Q.; Boukouvalas, J.
    Tetrahedron Lett.1990, 31, 995-998
  1. "A Short, Simple Synthesis of (±)-Monomorine"
    Jefford, C. W.; Tang, Q.; Zaslona, A.
    Helv. Chim. Acta1989, 72, 1749-1752
  1. "Sulfur-containing polybromoindoles from the red alga Laurencia brongniartii"
    Tanaka, J.; Higa, T.; Bernardinelli, G.; Jefford, C. W.
    Tetrahedron1989, 45, 7301-7310
  1. "The regio- and stereo-controlled synthesis of cis-p-menth-3-ene-1,2-diol by means of a 1,2,4-trioxane intermediate"
    Jefford, C. W.; Jaber, A.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1989, 1916-1918
  1. "In vitro effects of three new 1,2,4-trioxanes (pentatroxane, thiahexatroxane, and hexatroxanone) on Toxoplasma gondii."
    Chang, H. R.; Jefford, C. W.; Pechère, J. C.
    Antimicrob. Agents Chemother.1989, 33, 1748-1752
  1. "Synthesis of cis and trans Whisky and Cognac lactones by the regiocontrolled alkylation of 2-(trimethylsiloxy)furan"
    Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J.
    Helv. Chim. Acta1989, 72, 1362-1370
  1. "Synthesis of tricyclic arteannuin-like compounds"
    Jefford, C. W.; Velarde, J.; Bernardinelli, G.
    Tetrahedron Lett.1989, 30, 4485-4488
  1. "Batzellines A, B, and C. Novel pyrroloquinoline alkaloids from the sponge Batzella Sp."
    Sakemi, S.; Sun, H. H.; Jefford, C. W.; Bernardinelli, G.
    Tetrahedron Lett.1989, 30, 2517-2520
  1. "Total synthesis of bromobeckerelide"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.
    Tetrahedron Lett.1989, 30, 1237-1240
  1. "1,2,4-Trioxanes as Masked, Dual Purpose, Functional Groups"
    W. Jefford, C.; Rossier, J.-C.; Boukouvalas, J.
    Heterocycles1989, 28, 673-676
  1. "New methodology for the synthesis of biologically active lactones"
    Jefford, C. W.; Jaggi, D.; Sledeski, A. W.; Boukouvalas, J.
    in Studies in Natural Products Chemistry vol 3; Atta-ur-Rahman, and F. (Ed.)Elsevier: Amsterdam, 1989; Part b; p. 157-171
  1. "Mechanistic and Synthetic Studies on the Formation of 1,2,4-Trioxanes Related to Arteannuin. Photooxygenation of a bicyclic dihydropyran"
    Jefford, C. W.; Wang, Y.; Bernardinelli, G.
    Helv. Chim. Acta1988, 71, 2042-2052
  1. "Regioselective aldol condensations of boron and tin furanolates with aldehydes: an improved synthesis of 2-(1'-hydroxyalkyl)butenolides"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1988, 1595-1596
  1. "Itomanindoles A and B. Methylsulfinylindoles from Laurencia Brongniartii"
    Tanaka, J.; Higa, T.; Bernardinelli, G.; Jefford, C. W.
    Tetrahedron Lett.1988, 29, 6091-6094
  1. "Synthesis of New 1,2,4-Trioxanes and their Antimalarial Activity"
    Jefford, C. W.; McGoran, E. C.; Boukouvalas, J.; Richardson, G.; Robinson, B. L.; Peters, W.
    Helv. Chim. Acta1988, 71, 1805-1812
  1. "Brianthein V, a New Cytotoxic and Antiviral Diterpene Isolated from Briareum asbestinum"
    Coval, S. J.; Cross, S.; Bernardinelli, G.; Jefford, C. W.
    J. Nat. Prod.1988, 51, 981-984
  1. "A Vibrational Study of Some 1,2,4-Trioxanes"
    Mohnhaupt, M.; Hagemann, H.; Perler, J.-P.; Bill, H.; Boukouvalas, J.; Rossier, J.-C.; Jefford, C. W.
    Helv. Chim. Acta1988, 71, 992-999
  1. "Selective, heterogeneous oxidation of alcohols and diols with potassium permanganate"
    Jefford, C. W.; Wang, Y.
    J. Chem. Soc., Chem. Commun.1988, 634-635
  1. "Efficient Preparation of 1,2,4,5-Tetroxanes from Bis(trimethylsilyl) Peroxide and Carbonyl Compounds"
    Jefford, C. W.; Jaber, A.; Boukouvalas, J.
    Synthesis1988, 391-393
  1. "Electronic control of the stereoselectivities of electrocyclic reactions of cyclobutenes against incredible steric odds"
    Houk, K. N.; Spellmeyer, D. C.; Jefford, C. W.; Rimbault, C. G.; Wang, Y.; Miller, R. D.
    J. Org. Chem.1988, 53, 2125-2127
  1. "Regioselective alkylation of 2-trimethylsiloxyfuran; direct access to 4-substituted but-2-en-4-olides"
    Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1988, 364-365
  1. "New applications of peroxides and their equivalents for synthesizing oxygen heterocycles"
    Jefford, C. W.
    Stud. Org. Chem. (Amsterdam)1988, 33, 13-22
  1. "Manzamine B and C, two novel alkaloids from the sponge haliclona sp."
    Sakai, R.; Kohmoto, S.; Higa, T.; Jefford, C. W.; Bernardinelli, G.
    Tetrahedron Lett.1987, 28, 5493-5496
  1. "A mild and efficient preparation of cis-1,2-diols from 1,2,4-trioxanes"
    Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1987, 1593-1594
  1. "A simple, general distereoselective synthesis of 5-hydroxyalkylbutan-4-olides"
    Jefford, C. W.; Wang, Y.
    J. Chem. Soc., Chem. Commun.1987, 1513-1514
  1. "Diastereoselectivity in the directed aldol condensation of 2-trimethylsiloxyfuran with aldehydes. A stereodivergent route to threo and erythro δ-hydroxy-γ-lactones"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.
    Tetrahedron Lett.1987, 28, 4037-4040
  1. "The synthesis of (±)-cavernosine"
    Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J.
    Tetrahedron Lett.1987, 28, 4041-4044
  1. "Electrophile-induced rearrangement of 1,2,4-trioxanes. Formation of 1-benzofuran and 2H-1-benzopyrans"
    Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1987, 713-714
  1. "Structures of an ozonide, a spirocyclic acetal and a hydroperoxide derived from cyclopenteno-1,2,4-trioxanes"
    Bernardinelli, G.; Jefford, C. W.; Boukouvalas, J.; Jaggi, D.; Kohmoto, S.
    Acta Crystallogr., Sect. C: Cryst. Struct. Commun.1987, 43, 701-705
  1. "The reaction of adamantylideneadamantane with singlet oxygen mediated by rose bengal and charge transfer complexes"
    Jefford, C. W.; Estrada, M. J.; Barchietto, G.
    Tetrahedron1987, 43, 1737-1745
  1. "A direct synthesis of (±)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran"
    Jefford, C. W.; Sledeski, A. W.; Boukouvalas, J.
    Tetrahedron Lett.1987, 28, 949-950
  1. "Mechanistic and synthetic studies pertaining to 1,2,4-trioxanes"
    Jefford, C. W.; Ferrufino, M.; Hatsui, T.; Favarger, F.; Jaggi, D.; Rossier, J.-C.; Ferro, S.; Velarde, J.; Kohmoto, S.; et al., .
    Stud. Org. Chem. (Amsterdam)1987, 31, 113-120
  1. "Intramolecular Carbenoid Reactions of Pyrrole Derivatives. A Total Synthesis of (±)-Ipalbidine"
    Jefford, C. W.; Kubota, T.; Zaslona, A.
    Helv. Chim. Acta1986, 69, 2048-2061
  1. "Eliminative ring fission of 1,2,4-trioxan-5-ones. A new approach to α-keto acids"
    Jefford, C. W.; Rossier, J.-C.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1986, 1701-1702
  1. "The Formation of Bridged Bicyclic 1,2,4-Trioxanes by Intramolecular Capture of β-Hydroperoxy Cations"
    Jefford, C. W.; Favarger, F.; Ferro, S.; Chambaz, D.; Bringhen, A.; Bernardinelli, G.; Boukouvalas, J.
    Helv. Chim. Acta1986, 69, 1778-1786
  1. "Manzamine A, a novel antitumor alkaloid from a sponge"
    Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G.
    J. Am. Chem. Soc.1986, 108, 6404-6405
  1. "Venustatriol. A new, anti-viral, triterpene tetracyclic ether from Laurencia venusta"
    Sakemi, S.; Higa, T.; Jefford, C. W.; Bernardinelli, G.
    Tetrahedron Lett.1986, 27, 4287-4290
  1. "A short, stereodivergent synthesis of the racemic erythro and threo diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.
    Tetrahedron Lett.1986, 27, 4011-4014
  1. "Intramolecular Oxygen Transfer on the Ozonolysis of a Diphenylcyclopentene Derivative"
    Jefford, C. W.; Boukouvalas, J.; Jaggi, D.; Kohmoto, S.; Bernardinelli, G.
    Helv. Chim. Acta1986, 69, 941-948
  1. "The Absolute Configurations and Biogenesis of Some New Halogenated Chamigrenes from the Sea Hare Aplysia dactylomela"
    Sakai, R.; Higa, T.; Jefford, C. W.; Bernardinelli, G.
    Helv. Chim. Acta1986, 69, 91-105
  1. "New chemistry involving 1,2,4-trioxanes related to Qinghaosu"
    Jefford, C. W.; Ferro, S.; Moulin, M. C.; Velarde, J.; Jaggi, D.; Kohmoto, S.; Richardson, G. D.; Godoy, J.; Rossier, J.-C.; Bernardinelli, G.; Boukouvalas, J.
    in New Trends in natural products chemistry; Atta-ur-Rahman, .; Le Quesne, and P. W. (Eds.)Studies in Organic Chemistry, 26; Overseas Publishers Association: Amsterdam, 1986; p. 163
  1. "Chemistry of 1,2,4-trioxanes. Formation of 1,2-diol monoesters"
    Jefford, C. W.; Kohmoto, S.; Rossier, J.-C.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1985, 1783-1784
  1. "Competitive intramolecular carbenoid reactions of pyrrole derivatives"
    Jefford, C. W.; Zaslona, A.
    Tetrahedron Lett.1985, 26, 6035-6038
  1. "Acid-Catalyzed Cleavage of 1,4-Dimethyl-1,4-dihydronaphthalene 1,4-Endoperoxide. Reactivity of the Resulting Hydroperoxy Carbocation with Nucleophiles"
    Jefford, C. W.; Rossier, J.-C.; Kohmoto, S.; Boukouvalas, J.
    Helv. Chim. Acta1985, 68, 1804-1814
  1. "The Reaction of Dihalocarbenes with Quadricyclane"
    Jefford, C. W.; Roussilhe, J.; Papadopoulos, M.
    Helv. Chim. Acta1985, 68, 1557-1568
  1. "New chemistry of zwitterionic peroxides arising by photooxygenation of enol ethers"
    Jefford, C. W.; Boukouvalas, J.; Kohmoto, S.; Bernardinelli, G.
    Tetrahedron1985, 41, 2081-2088
  1. "An unusual stereospecific epoxidation with “per-amberlyst 15®”"
    Jefford, C. W.; Bernardinelli, G.; Rossier, J.-C.; Kohmoto, S.; Boukouvalas, J.
    Tetrahedron Lett.1985, 26, 615-618
  1. "A New Approach to Bicyclic 1,3-Dioxolanes: Acetalization of γ-Hydroxycyclohexenones"
    Jefford, C. W.; Rossier, J.-C.; Kohmoto, S.; Boukouvalas, J.
    Synthesis1985, 29-31
  1. "Determination of the thermal stability of some 1,2-dioxetanes by high-performance liquid chromatography"
    Jefford, C. W.; Grant, H. G.; Kohmoto, S.; Boukouvalas, J.
    J. Chromatogr., A1985, 347, 183-187
  1. "An improved method for high-performance liquid chromatography of gossypol"
    Jefford, C. W.; Grant, H. G.
    Anal. Chim. Acta1985, 166, 311-314
  1. "A New Approach to 1,2,4-Trioxanes form Cyclic Allylic Hydroperoxides"
    Jefford, C. W.; Jaggi, D.; Kohmoto, S.; Boukouvalas, J.; Bernardinelli, G.
    Helv. Chim. Acta1984, 67, 2254-2260
  1. "Effect of Substituents, Solvent, and Temperature on the Reactivity of the Zwitterionic Peroxides Arising from the Photo-Oxygenation of 2-(Methoxymethylidene)- and 2-(Phenoxymethylidene)adamantane"
    Jefford, C. W.; Grant, H. G.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S.
    Helv. Chim. Acta1984, 67, 2210-2217
  1. "An Efficient Synthesis of 1,4-Dichlorobicyclo[2.2.1]heptan-2-one"
    Jefford, C. W.; Barchietto, G.
    Synthesis1984, 1012-1014
  1. "Heterogeneous chirality transfer on photooxygenation"
    Gerdil, R.; Barchietto, G.; Jefford, C. W.
    J. Am. Chem. Soc.1984, 106, 8004-8005
  1. "The Reaction of 4-Hydroperoxy-2,4,6-trimethylcyclohexa-2,5-dienone with Acetaldehyde. Formatino of the Bis(peroxyacetal)"
    Jefford, C. W.; Bernardinelli, G.; McGoran, E. C.
    Helv. Chim. Acta1984, 67, 1952-1956
  1. "Functionalization of the methyl group of 1,4-dimethyl-1,4-dihydronaphthalene-1,4-endoperoxide"
    Jefford, C. W.; Rossier, J.-C.; Kohmoto, S.; Boukouvalas, J.
    J. Chem. Soc., Chem. Commun.1984, 1496-1497
  1. "Dynamic molecular modeling. The case of rearranging polycyclic C8H9 cations"
    Jefford, C. W.; Mareda, J.; Combremont, J. J.; Weber, J.
    CHIMIA1984, 38, 354-356
  1. "The Reaction of Singlet Oxygen with 1,3-Dimethylindole in the Presence of Aldehydes. Formation of 1,2,4-Trioxanes"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S.; Bernardinelli, G.
    Helv. Chim. Acta1984, 67, 1104-1111
  1. "Reactions of cyclic peroxides with aldehydes and ketones catalysed by trimethylsilyl trifluoromethanesulphonate. An efficient synthesis of 1,2,4-trioxanes"
    Jefford, C. W.; Boukouvalas, J.; Kohmoto, S.
    J. Chem. Soc., Chem. Commun.1984, 523-524
  1. "High-performance liquid chromatography of some novel diastereomeric tricyclic 1,2,4-trioxanes"
    Jefford, C. W.; Boukouvalas, J.; Kohmoto, S.; Grant, H. G.
    Anal. Chim. Acta1984, 157, 199-202
  1. "Intramolecular Carbenoid Reactions of Pyrrole Derivatives Efficient Syntheses of Pyrrolizinone and Dihydroindolizinone"
    Jefford, C. W.; Johncock, W.
    Helv. Chim. Acta1983, 66, 2666-2671
  1. "A New Reaction of 1,2-Dioxetanes. Formation of 1,2,4-Trioxanes from Aldehydes"
    Jefford, C. W.; Boukouvalas, J.; Kohmoto, S.
    Helv. Chim. Acta1983, 66, 2615-2620
  1. "The reaction of trimethylsilyl α-trimethylsilylperoxy esters with ketones and aldehydes. A simple, efficient synthesis of 1,2,4-trioxan-5-ones"
    Jefford, C. W.; Rossier, J.-C.; Richardson, G. D.
    J. Chem. Soc., Chem. Commun.1983, 1064-1065
  1. "Reaction of singlet oxygen with enol ethers in the presence of acetaldehyde. Formation of 1,2,4-trioxanes"
    Jefford, C. W.; Kohmoto, S.; Boukouvalas, J.; Burger, U.
    J. Am. Chem. Soc.1983, 105, 6498-6499
  1. "Reaction of bicyclic endo peroxides with carbonyl compounds. A new approach to 1,2,4-trioxanes"
    Jefford, C. W.; Jaggi, D.; Boukouvalas, J.; Kohmoto, S.
    J. Am. Chem. Soc.1983, 105, 6497-6498
  1. "Ionization potentials, electron affinities, and molecular orbitals of 2-substituted norbornadienes. Theory of 1,2 and homo-1,4 carbene cycloaddition selectivities"
    Houk, K. N.; Rondan, N. G.; Paddon-Row, M. N.; Jefford, C. W.; Huy, P. T.; Burrow, P. D.; Jordan, K. D.
    J. Am. Chem. Soc.1983, 105, 5563-5569
  1. "Evidence for homoquadricyclene, a possible carbon ylide"
    Jefford, C. W.; Rossier, J.-C.; Zuber, J. A.; Kennard, O.; Cruse, W. B. T.
    Tetrahedron Lett.1983, 24, 181-184
  1. "Rearrangements Involving C8H8

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