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Total synthesis of drimane sesquiterpenes from S-(+)-carvone (part 5)

✍ Scribed by Henk J. Swarts; Anja A. Verstegen-Haaksma; Ben J.M. Jansen; Aede de Groot

Book ID: 104204872
Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 881 KB
Volume: 50
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)89624-1

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✦ Synopsis

AbstmeI: Coniue addition of wtassium cyanide to S-f+karvone followed bv anndation with me&y1 vinyl l&&e gave kern nikile 4 in hi& yield. Me@ation of 4. removal if the kqnqtcnyl groupandthcintroduccionoTc-12viaf~ylationthen~wthe lmsahualedketol&%one21whichis an excellent intemdiate in the iocal synthesis of dfima& squiteqenes. This was demonstrated with the toml synthds of 3fkcetoxydrimenin 24.

The insect antifeedant properties of drimane sesquiterpenes. e.g., polygodial and the related coloratanes, e.g., muzigadial (figure 1) are well known2. This interesting biological activity has greatly stimulated the

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