Determination by Asymmetric Total Synthesis of the Absolute Configuration of Lucilactaene, a Cell‐Cycle Inhibitor in p53‐Transfected Cancer Cells | Zendy

Yamaguchi Junichiro | Zendy; Kakeya Hideaki | Zendy; Uno Takao | Zendy; Shoji Mitsuru | Zendy; Osada Hiroyuki | Zendy; Hayashi Yujiro | Zendy

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Determination by Asymmetric Total Synthesis of the Absolute Configuration of Lucilactaene, a Cell‐Cycle Inhibitor in p53‐Transfected Cancer Cells

Author(s) -

Yamaguchi Junichiro,

Kakeya Hideaki,

Uno Takao,

Shoji Mitsuru,

Osada Hiroyuki,

Hayashi Yujiro

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200500060

Subject(s) - racemization , chemistry , absolute configuration , natural product , stereoselectivity , stereochemistry , transfection , combinatorial chemistry , biochemistry , gene , catalysis

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.

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