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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.