A Novel Carbon-Carbon Bond-Forming Reaction of Triflates with Copper(I)-Catalyzed Grignard Reagents. A New Concise and Enantiospecific Synthesis of (+)-exo-Brevicomin, (5R,6S)-(-)-6-Acetoxy-5-hexadecanolide, and L-Factor

Hiyoshizo Kotsuki, Isao Kadota, Masamitsu Ochi

Research output: Contribution to journalArticlepeer-review

83 Citations (Scopus)

Abstract

We describe here a full account of a highly concise and enantiospecific synthesis of (+)-exo-brevicomin (7), (5R,6S)-(-)-6-acetoxy-5-hexadecanolide (11), and L-factor (16) originating from d- or L-tartrates as chiral sources. The synthesis employs an efficient carbon—carbon bond-forming reaction of triflates with copper(I)-catalyzed Grignard reagents and, as a consequence, tosyl—triflate derivatives 6 and 15 were found to be a versatile intermediate. This methodology completed the synthetic scheme involving a five-step sequence from 1 to 7, a 10-step sequence from 2 to 11, and a seven-step sequence from 12 to 16. The results present a new rapid means to derive optically active natural products from readily available chiral building blocks.

Original languageEnglish
Pages (from-to)4417-4422
Number of pages6
JournalJournal of Organic Chemistry
Volume55
Issue number14
DOIs
Publication statusPublished - 1990
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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