Total synthesis of attenols A and B

Keisuke Araki, Kiyotake Suenaga, Tetsuya Sengoku, Daisuke Uemura

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

The enantioselective synthesis of attenols A and B, cyclic polyethers of marine origin, was accomplished on a semigram scale by using diastereoselective hydroboration, coupling with lithium acetylide, Lindlar reduction and acid-catalyzed acetal formation. The configuration of the remaining undetermined spiro acetal carbon was unambiguously determined to be 11S using this ample supply of attenol A. The antitumor activities of synthetic attenol A were also examined.

Original languageEnglish
Pages (from-to)1983-1995
Number of pages13
JournalTetrahedron
Volume58
Issue number10
DOIs
Publication statusPublished - 2002 Mar 4
Externally publishedYes

Keywords

  • Biological studies
  • Diastereoselective hydroboration
  • Enantioselective synthesis
  • Semigram scale
  • Stereochemistry of spiro acetal ring

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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