Determination by asymmetric total synthesis of the absolute configuration of lucilactaene, a cell-cycle inhibitor in p53-transfected cancer cells

Junichiro Yamaguchi, Hideaki Kakeya, Takao Uno, Mitsuru Shoji, Hiroyuki Osada, Yujiro Hayashi

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

(Chemical Equation Presented) A biomimetic pathway to lucilactaene (1) from NG-391 has been developed which involves stereoselective reactions under very mild conditions. It was demonstrated that 1 racemizes rapidly, and the conditions under which racemization occurs were elucidated. Lucilactaene (1) isolated under neutral conditions is racemic, which suggests that either the natural product is racemized rapidly in the mycelia, or racemic 1 is biosynthesized.

Original languageEnglish
Pages (from-to)3110-3115
Number of pages6
JournalAngewandte Chemie - International Edition
Volume44
Issue number20
DOIs
Publication statusPublished - 2005 May 13

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Keywords

  • Asymmetric synthesis
  • Biosynthesis
  • Lucilactaene
  • Racemization
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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