Transannular Cyclization in Cyclodecenes: The Case Study of Melampolides

200318 citationsJournal Article

Authors

Antonio Guerriero · University of Trento

Michele D’Ambrosio · University of Trento

Abstract

Abstract The structures of products formed by electrophilic transannular cyclization (ETC) in medium‐ring compounds are affected by several parameters. The melampolides, ( cis , trans )‐cyclodeca‐1(10),5‐diene terpenes, undergo ring closure only under Lewis acid conditions. The transannular distance proves to be a key factor. Molecular mechanics calculations suggest that the cis ring junction of products is formed through a less populated conformer. ETC has chemical significance because it may play an important role in the pharmacological action of sesquiterpene lactones. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Topics & Keywords

Sesquiterpenes and Asteraceae Studies Plant biochemistry and biosynthesis Natural product bioactivities and synthesis

Publication Details

Published in: European Journal of Organic Chemistry

Volume 2003, Issue 20, pp. 3969-3975

DOI: 10.1002/ejoc.200300315

Field-Weighted Citation Impact: 0.39

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Transannular Cyclization in Cyclodecenes: The Case Study of Melampolides

Authors

Abstract

Topics & Keywords

Publication Details