Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-β-eudesmol

Eugene A Mash, James A. Fryling

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22 Citations (Scopus)

Abstract

An enantioselective preparation of (+)-β-eudesmol employing a diastereoselective Simmons-Smith cyclopropanation is described. Cyclopropanation of a bicyclic enone precursor is directed by use of the corresponding (2S,3S)-2,3-butanediol ketal. The overall yield of (+)-β-eudesmol (75% ee) from racemic 7-carbomethoxy-3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one is 25% over eight steps.

Original languageEnglish (US)
Pages (from-to)3000-3003
Number of pages4
JournalJournal of Organic Chemistry
Volume52
Issue number14
StatePublished - 1987

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2,3-butylene glycol

ASJC Scopus subject areas

  • Organic Chemistry

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Homochiral ketals in organic synthesis. Enantioselective synthesis of (+)-β-eudesmol. / Mash, Eugene A; Fryling, James A.

In: Journal of Organic Chemistry, Vol. 52, No. 14, 1987, p. 3000-3003.

Research output: Contribution to journalArticle

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