A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

Benjamin E. Stephens; Fei Liu

doi:10.1016/j.tetlet.2007.10.141

A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

Benjamin E. Stephens, Fei Liu^*

^*Corresponding author for this work

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

6 Citations (Scopus)

Abstract

A multi-gram synthesis of a substituted α,β-unsaturated δ-lactone synthon, 1, was developed from commercially available d-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1.

Original language	English
Pages (from-to)	9116-9119
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	52
DOIs	https://doi.org/10.1016/j.tetlet.2007.10.141
Publication status	Published - 24 Dec 2007

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10.1016/j.tetlet.2007.10.141

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title = "A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon",

abstract = "A multi-gram synthesis of a substituted α,β-unsaturated δ-lactone synthon, 1, was developed from commercially available d-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1.",

author = "Stephens, {Benjamin E.} and Fei Liu",

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AU - Stephens, Benjamin E.

AU - Liu, Fei

PY - 2007/12/24

Y1 - 2007/12/24

N2 - A multi-gram synthesis of a substituted α,β-unsaturated δ-lactone synthon, 1, was developed from commercially available d-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1.

AB - A multi-gram synthesis of a substituted α,β-unsaturated δ-lactone synthon, 1, was developed from commercially available d-galactose. The use of a Horner-Wadsworth-Emmons reaction was able to furnish, with Z selectivity, the enone ester that spontaneously lactonised to provide enantiomerically pure 1.

UR - http://www.scopus.com/inward/record.url?scp=36448957971&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2007.10.141

DO - 10.1016/j.tetlet.2007.10.141

M3 - Article

AN - SCOPUS:36448957971

SN - 0040-4039

VL - 48

SP - 9116

EP - 9119

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 52

ER -

A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

Abstract

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