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Synthesis of macrocyclic terpenoids by intramolecular cyclization XIII. : Stereoselective synthesis of (±)-cubitene, a component of defense secretion of termites

✍ Scribed by Mitsuaki Kodama; Toshiya Takahashi; Tsutomu Kojima; Sho Ito

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 722 KB
Volume: 44
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)86074-9

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✦ Synopsis

Stereoselective synthesis of cubitene (11, a novel diterp-ene isolated from defense secretion of termites, has been accomplished using an intramolecular reaction of a-sulfenyl carbanion vi th epoxide. Hydride reduction of the ketone 11 obtalned by Claisen rearrangement occurred in unexpectedly high stereoselectivlty yielding the chlorohydrln 12 with the desired stereochemistry.

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