Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol

Ken S. Feldman, Robert E. Simpson

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

(E)-Selective oxygenation of 1,2-disubstituted alkenylcyclopropanes, and subsequent SmI 2 mediated cleavage of the 1,2-dioxolane products with retention of stereochemistry, leads to a concise synthesis of the plant metabolite (±)-yashabushitriol.

Original languageEnglish (US)
Pages (from-to)6985-6988
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number50
DOIs
StatePublished - Jan 1 1989

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Dioxolanes
Stereochemistry
Oxygenation
Metabolites
formal glycol
samarium diiodide

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol. / Feldman, Ken S.; Simpson, Robert E.

In: Tetrahedron Letters, Vol. 30, No. 50, 01.01.1989, p. 6985-6988.

Research output: Contribution to journalArticle

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