A stereoselective synthesis of the C(3)-C(13) and C(14)-C(24) fragments of macrolactin A

Shu Kun Li, Rui Xu, Xiang Shu Xiao, Dong Lu Bai

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

Synthetic studies towards the C(3)-C(13) and C(14)-C(24) segments (3,4) of the potent antiviral and antitumor compound macrolactin A (1) are presented. Compound 3 was constructed via a convergent and facile approach, exploiting Wittig olefination to generate the sensitive E, Z-diene moiety. Compound 4 was synthesized from the chiral-pool derived sulfone 39a via an α-alkylation-desulfonation reaction sequence. Cu(II)-catalyzed coupling of a Grignard reagent with an allylic bromide and Julia olefination were also investigated for the preparation of compound 4.

Original languageEnglish (US)
Pages (from-to)910-923
Number of pages14
JournalChinese Journal of Chemistry
Volume18
Issue number6
StatePublished - Dec 1 2000

Keywords

  • Antiviral
  • Julia olefination
  • Macrolactin A
  • Stereoselective synthesis
  • Sulfone alkylation
  • Wittig reaction

ASJC Scopus subject areas

  • Chemistry(all)

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