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 journalArticle

10 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)11291-11298
Number of pages8
JournalTetrahedron
Volume61
Issue number47
DOIs
StatePublished - Nov 21 2005
Externally publishedYes

Fingerprint

Organophosphonates
Sulfones
Alkylation
Anions
macrolactin A
allyl bromide

Keywords

  • Horner-Emmons reaction
  • Macrolactin A
  • seco-Precursor

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A convergent and stereoselective synthesis of a seco-precursor of macrolactin A. / Li, Shukun; Xiao, Xiangshu; Yan, Xuebin; Liu, Xuejun; Xu, Rui; Bai, Donglu.

In: Tetrahedron, Vol. 61, No. 47, 21.11.2005, p. 11291-11298.

Research output: Contribution to journalArticle

Li, Shukun ; Xiao, Xiangshu ; Yan, Xuebin ; Liu, Xuejun ; Xu, Rui ; Bai, Donglu. / A convergent and stereoselective synthesis of a seco-precursor of macrolactin A. In: Tetrahedron. 2005 ; Vol. 61, No. 47. pp. 11291-11298.
@article{b47352e0a03f4cfd802edeec4114928f,
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",
year = "2005",
month = "11",
day = "21",
doi = "10.1016/j.tet.2005.07.106",
language = "English (US)",
volume = "61",
pages = "11291--11298",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "47",

}

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

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

UR - http://www.scopus.com/inward/record.url?scp=27144542731&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27144542731&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2005.07.106

DO - 10.1016/j.tet.2005.07.106

M3 - Article

VL - 61

SP - 11291

EP - 11298

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 47

ER -