Synthetic studies on apoptolidin: Synthesis of the C12-C28 fragment via a highly stereoselective aldol reaction

Kazuyuki Abe, Koji Kato, Tadamasa Arai, Mohammad Abdur Rahim, Israt Sultana, Shuichi Matsumura, Kazunobu Toshima

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

The stereoselective and convergent synthesis of the C12-C28 segment 2 of the apoptosis inducing macrolide antibiotic, apoptolidin (1), is described. The synthesis involves a highly stereoselective tin(II)-mediated aldol reaction between the C17-C22 ethyl ketone 3 and the C23-C28 aldehyde 4 as the key step.

Original languageEnglish
Pages (from-to)8849-8853
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number48
DOIs
Publication statusPublished - 2004 Nov 22

Keywords

  • Aldol reaction
  • Antibiotic
  • Apoptolidin
  • Apoptosis
  • Macrolide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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