A novel alkynylation reaction of epoxy alcohols: Use in the synthesis of erythro-6-acetoxyhexadecan-5-olide

Masahiko Yamaguchi; Ichiro Hirao

doi:10.1039/c39840000202

A novel alkynylation reaction of epoxy alcohols: Use in the synthesis of erythro-6-acetoxyhexadecan-5-olide

Masahiko Yamaguchi, Ichiro Hirao

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

37 Citations (Scopus)

Abstract

Lithium acetylides in the presence of BF₃·Et₂O react with epoxy alcohols derived from (E)-allylic alcohols to give erythro-1,2-diols, a reaction used successfully in the stereoselective synthesis of erythro-hexadecan-5-olide.

Original language	English
Pages (from-to)	202-203
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	3
DOIs	https://doi.org/10.1039/c39840000202
Publication status	Published - 1984 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Molecular Medicine

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title = "A novel alkynylation reaction of epoxy alcohols: Use in the synthesis of erythro-6-acetoxyhexadecan-5-olide",

abstract = "Lithium acetylides in the presence of BF3·Et2O react with epoxy alcohols derived from (E)-allylic alcohols to give erythro-1,2-diols, a reaction used successfully in the stereoselective synthesis of erythro-hexadecan-5-olide.",

author = "Masahiko Yamaguchi and Ichiro Hirao",

year = "1984",

month = jan,

day = "1",

doi = "10.1039/c39840000202",

language = "English",

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journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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AU - Yamaguchi, Masahiko

AU - Hirao, Ichiro

PY - 1984/1/1

Y1 - 1984/1/1

N2 - Lithium acetylides in the presence of BF3·Et2O react with epoxy alcohols derived from (E)-allylic alcohols to give erythro-1,2-diols, a reaction used successfully in the stereoselective synthesis of erythro-hexadecan-5-olide.

AB - Lithium acetylides in the presence of BF3·Et2O react with epoxy alcohols derived from (E)-allylic alcohols to give erythro-1,2-diols, a reaction used successfully in the stereoselective synthesis of erythro-hexadecan-5-olide.

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A novel alkynylation reaction of epoxy alcohols: Use in the synthesis of erythro-6-acetoxyhexadecan-5-olide

Abstract

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