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

doi:10.1016/S0040-4039(01)93404-5

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

Chemistry

Research output: Contribution to journal › Article › peer-review

50 Scopus citations

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 language	English (US)
Pages (from-to)	6985-6988
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	50
DOIs	https://doi.org/10.1016/S0040-4039(01)93404-5
State	Published - Jan 1 1989

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)93404-5

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

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.",

author = "Feldman, \{Ken S.\} and Simpson, \{Robert E.\}",

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AU - Feldman, Ken S.

AU - Simpson, Robert E.

PY - 1989/1/1

Y1 - 1989/1/1

N2 - (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.

AB - (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.

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UR - https://www.scopus.com/pages/publications/0024803953#tab=citedBy

U2 - 10.1016/S0040-4039(01)93404-5

DO - 10.1016/S0040-4039(01)93404-5

M3 - Article

AN - SCOPUS:0024803953

SN - 0040-4039

VL - 30

SP - 6985

EP - 6988

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 50

ER -

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

Abstract

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