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

23 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
Externally publishedYes

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Biomimetics
Cells
Biological Products
lucilactaene

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Determination by asymmetric total synthesis of the absolute configuration of lucilactaene, a cell-cycle inhibitor in p53-transfected cancer cells. / Yamaguchi, Junichiro; Kakeya, Hideaki; Uno, Takao; Shoji, Mitsuru; Osada, Hiroyuki; Hayashi, Yujiro.

In: Angewandte Chemie - International Edition, Vol. 44, No. 20, 13.05.2005, p. 3110-3115.

Research output: Contribution to journalArticle

Yamaguchi, Junichiro ; Kakeya, Hideaki ; Uno, Takao ; Shoji, Mitsuru ; Osada, Hiroyuki ; Hayashi, Yujiro. / Determination by asymmetric total synthesis of the absolute configuration of lucilactaene, a cell-cycle inhibitor in p53-transfected cancer cells. In: Angewandte Chemie - International Edition. 2005 ; Vol. 44, No. 20. pp. 3110-3115.
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