Reinvestigation of the stereochemistry of kulokekahilide-2

Yuuki Takada, Eriko Mori, Masahiro Umehara, Yoichi Nakao, Junji Kimura

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

An attempt to carry out a total synthesis of kulokekahilide-2 (1) by macrolactonization of a seco acid prepared from a suitably protected hexapeptide and a dioxy acid moiety unexpectedly resulted in the formation of the 43-epimer (1a) of the cytotoxic depsipeptide, for which structure 1b has previously been proposed. A second attempt involving macrolactamization of the corresponding amino acid gave the target product, 1b, but the spectral data of the product did not match those of natural 1. Furthermore, neither 1a nor 1b showed any cytotoxicity, from which it is concluded that the structure of natural 1 is incorrect and should be re-examined.

Original languageEnglish
Pages (from-to)7653-7656
Number of pages4
JournalTetrahedron Letters
Volume48
Issue number43
DOIs
Publication statusPublished - 2007 Oct 22

Keywords

  • 43-epi-Kulokekahilide-2
  • Cytotoxicity
  • Kulokekahilide-2

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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