Stereochemical assignment of topsentolide C2 by stereodivergent synthesis of its four diastereomers

Ryo Towada, Yusuke Kurashina, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Four diastereomers of topsentolide C2, a cytotoxic 9-membered lactone isolated from the marine sponge Topsentia sp., were synthesized stereodivergently from a common chiral seco acid by the combined use of the Yamaguchi and Mitsunobu lactonizations. Comparison of the NMR spectra of the four diastereomers with those of an authentic sample of topsentolide C2 led to the stereochemical determination of topsentolide C2 as 8R, 11S and 12S.

Original languageEnglish
Pages (from-to)6878-6881
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number50
DOIs
Publication statusPublished - 2013 Dec 11

Keywords

  • Cytotoxic
  • Lactonization
  • Oxylipin
  • Topsentolide
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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