Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

Akira Morita; Shigefumi Kuwahara

doi:10.1016/j.tetlet.2007.03.055

Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

Akira Morita, Shigefumi Kuwahara

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20 Citations (Scopus)

Abstract

A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.

Original language	English
Pages (from-to)	3163-3166
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2007.03.055
Publication status	Published - 2007 Apr 30

Keywords

2,4-Alkadienoic acid
Antibiotic
Cross-metathesis
Elaiolide
Enantioselective synthesis

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2007.03.055

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title = "Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide",

abstract = "A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.",

keywords = "2,4-Alkadienoic acid, Antibiotic, Cross-metathesis, Elaiolide, Enantioselective synthesis",

author = "Akira Morita and Shigefumi Kuwahara",

note = "Funding Information: We thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 16380075).",

year = "2007",

month = apr,

day = "30",

doi = "10.1016/j.tetlet.2007.03.055",

language = "English",

volume = "48",

pages = "3163--3166",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "18",

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T1 - Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

AU - Morita, Akira

AU - Kuwahara, Shigefumi

N1 - Funding Information: We thank Ms. Yamada (Tohoku University) for measuring NMR and MS spectra. This work was supported, in part, by a Grant-in-Aid for Scientific Research (B) from the Ministry of Education, Culture, Sports, Science and Technology of Japan (No. 16380075).

PY - 2007/4/30

Y1 - 2007/4/30

N2 - A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.

AB - A (2E,4E)-7-hydroxy-2,4-dienoic acid, previously employed as a key intermediate for the total synthesis of the macrodiolide antibiotic elaiolide, was prepared stereoselectively and concisely from (S)-2-methyl-3-trityloxypropanal by a three-step sequence consisting of Brown's asymmetric crotylboration, olefin cross-metathesis, and alkaline treatment. Ethyl 3-pivaloyloxy-4-pentenoate was used as a masked dienoate in the cross-metathesis step.

KW - 2,4-Alkadienoic acid

KW - Antibiotic

KW - Cross-metathesis

KW - Elaiolide

KW - Enantioselective synthesis

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DO - 10.1016/j.tetlet.2007.03.055

M3 - Article

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VL - 48

SP - 3163

EP - 3166

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 18

ER -

Cross-metathesis approach to a (2E,4E)-dienoic acid intermediate for the synthesis of elaiolide

Abstract

Keywords

ASJC Scopus subject areas

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