A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

Shukun Li; Xiangshu Xiao; Xuebin Yan; Xuejun Liu; Rui Xu; Donglu Bai

doi:10.1016/j.tet.2005.07.106

A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

Shukun Li, Xiangshu Xiao, Xuebin Yan, Xuejun Liu, Rui Xu, Donglu Bai

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

11 Scopus citations

Abstract

A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C₁-C₁₀ segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The α-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C₁₁-C₂₄ segment.

Original language	English (US)
Pages (from-to)	11291-11298
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2005.07.106
State	Published - Nov 21 2005
Externally published	Yes

Keywords

Horner-Emmons reaction
Macrolactin A
seco-Precursor

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.07.106

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title = "A convergent and stereoselective synthesis of a seco-precursor of macrolactin A",

abstract = "A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C1-C10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The α-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C11-C24 segment.",

keywords = "Horner-Emmons reaction, Macrolactin A, seco-Precursor",

author = "Shukun Li and Xiangshu Xiao and Xuebin Yan and Xuejun Liu and Rui Xu and Donglu Bai",

note = "Funding Information: This work was supported by a grant from the National Natural Science Foundation of China and a grant from the State Key Laboratory of Bio-organic and Natural Products Chemistry.",

year = "2005",

month = nov,

day = "21",

doi = "10.1016/j.tet.2005.07.106",

language = "English (US)",

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TY - JOUR

T1 - A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

AU - Li, Shukun

AU - Xiao, Xiangshu

AU - Yan, Xuebin

AU - Liu, Xuejun

AU - Xu, Rui

AU - Bai, Donglu

N1 - Funding Information: This work was supported by a grant from the National Natural Science Foundation of China and a grant from the State Key Laboratory of Bio-organic and Natural Products Chemistry.

PY - 2005/11/21

Y1 - 2005/11/21

N2 - A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C1-C10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The α-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C11-C24 segment.

AB - A seco-precursor of macrolactin A was synthesized by coupling two advanced segments. Wittig reaction and Horner-Emmons reaction were utilized to construct the three characteristic E,Z and E,E dienes. The C1-C10 segment was synthesized through Horner-Emmons reaction with phosphonate reagent. The α-alkylation of sulfone stabilized anion with allyl bromide followed by desulfonation gave the C11-C24 segment.

KW - Horner-Emmons reaction

KW - Macrolactin A

KW - seco-Precursor

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DO - 10.1016/j.tet.2005.07.106

M3 - Article

AN - SCOPUS:27144542731

SN - 0040-4020

VL - 61

SP - 11291

EP - 11298

JO - Tetrahedron

JF - Tetrahedron

IS - 47

ER -

A convergent and stereoselective synthesis of a seco-precursor of macrolactin A

Abstract

Keywords

ASJC Scopus subject areas

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