The Journal of Organic Chemistry

A highly stereoselective synthesis of podophyllotoxin and analogues based on an intramolecular Diels-Alder reaction

DI Macdonald, T Durst

Index: Macdonald, D.I.; Durst, T. Journal of Organic Chemistry, 1988 , vol. 53, # 16 p. 3663 - 3669

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Citation Number: 41

Abstract

A synthesis of podophyllotoxin and several analogues is described. The key step that generates all four chiral centers of podophyllotoxin involves an intramolecular Diels-Alder reaction between an appropriately substituted o-quinodimethane and a pendant crotonate moiety. Thus trans-2-(3, 4, 5-trimethoxyphenyl)-4, 5-(methylenedi-oxy) benzocyclobutenol (7) was coupled with the isocyanate derived from methyl trans-4-aminocrotonate to yield ...