Homochiral ketals in organic synthesis. Enantioselective synthesis of (R)-muscone

Keith A. Nelson, Eugene A Mash

Research output: Contribution to journalArticle

58 Citations (Scopus)

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
StatePublished - 1986

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Chelation
muscone
tartaric acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Homochiral ketals in organic synthesis. Enantioselective synthesis of (R)-muscone. / Nelson, Keith A.; Mash, Eugene A.

In: Journal of Organic Chemistry, Vol. 51, No. 14, 1986, p. 2721-2724.

Research output: Contribution to journalArticle

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