Homochiral Ketals in Organic Synthesis. Enantioselective Synthesis of (R)-Muscone

Keith A. Nelson, Eugene A. Mash

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

An efficient, enantioselective preparation of (R)-muscone employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation is directed via chelation control by a homochiral ketal protecting group derived from unnatural tartaric acid. The overall yield of (R)-muscone (>95% R) from commercially available cyclopentadecanone is 60% over seven steps.

Original languageEnglish (US)
Pages (from-to)2721-2724
Number of pages4
JournalJournal of Organic Chemistry
Volume51
Issue number14
DOIs
StatePublished - Jan 1 1986

    Fingerprint

ASJC Scopus subject areas

  • Organic Chemistry

Cite this