Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols: Total synthesis of (+)-prelactone C

Tomoyuki Esumi; Hiroko Fukuyama; Reiko Oribe; Kaori Kawazoe; Yoshiharu Iwabuchi; Hiroshi Irie; Susumi Hatakeyama

doi:10.1016/S0040-4039(97)01042-3

Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols: Total synthesis of (+)-prelactone C

Tomoyuki Esumi, Hiroko Fukuyama, Reiko Oribe, Kaori Kawazoe, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

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

23 Citations (Scopus)

Abstract

A concise method leading to all stereoisomers of 1-benzyloxy-3-methyl-6-heptene-2,4-diol from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol has been developed. The first synthesis of (+)-prelactone C, a δ-lactone isolated from the concanamycin-producing Streptomyces sp., has been achieved utilizing (2S,3S,4R)-1-benzyloxy-3-methyl-6-heptene-2,4-diol as a chiral building block.

Original language	English
Pages (from-to)	4823-4826
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(97)01042-3
Publication status	Published - 1997 Jul 7
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols : Total synthesis of (+)-prelactone C. / Esumi, Tomoyuki; Fukuyama, Hiroko; Oribe, Reiko; Kawazoe, Kaori; Iwabuchi, Yoshiharu; Irie, Hiroshi; Hatakeyama, Susumi.

In: Tetrahedron Letters, Vol. 38, No. 27, 07.07.1997, p. 4823-4826.

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

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abstract = "A concise method leading to all stereoisomers of 1-benzyloxy-3-methyl-6-heptene-2,4-diol from (2E,5E)-1,7-dibenzyloxy-2,5-heptadiene-4-ol has been developed. The first synthesis of (+)-prelactone C, a δ-lactone isolated from the concanamycin-producing Streptomyces sp., has been achieved utilizing (2S,3S,4R)-1-benzyloxy-3-methyl-6-heptene-2,4-diol as a chiral building block.",

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AU - Oribe, Reiko

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AU - Hatakeyama, Susumi

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