TY - JOUR
T1 - Determination by asymmetric total synthesis of the absolute configuration of lucilactaene, a cell-cycle inhibitor in p53-transfected cancer cells
AU - Yamaguchi, Junichiro
AU - Kakeya, Hideaki
AU - Uno, Takao
AU - Shoji, Mitsuru
AU - Osada, Hiroyuki
AU - Hayashi, Yujiro
PY - 2005/5/13
Y1 - 2005/5/13
N2 - (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.
AB - (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.
KW - Asymmetric synthesis
KW - Biosynthesis
KW - Lucilactaene
KW - Racemization
KW - Total synthesis
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U2 - 10.1002/anie.200500060
DO - 10.1002/anie.200500060
M3 - Article
C2 - 15832392
AN - SCOPUS:18844398098
SN - 1433-7851
VL - 44
SP - 3110
EP - 3115
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 20
ER -
