Synthesis, stereochemistry confirmation and biological activity evaluation of a constituent from Isodon excisus

A synthesis and stereochemistry confirmation of a constituent recently isolated from the whole plant Isodon excisus is reported. An enantioselective catalytic boron-mediated reduction of an α-bromoketone was utilized in the key synthetic transformation. The methodology described herein was also used...

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Bibliographic Details
Published in:Tetrahedron 2003-12, Vol.59 (50), p.9961-9969
Main Authors: Xing, Xuechao, Ho, Pei, Bourquin, Geoffroy, Yeh, Li-An, Cuny, Gregory D
Format: Article
Language:English
Subjects:
apoptosis
boron
caspase-induction
inhibitor
Isodon excisus
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Summary:A synthesis and stereochemistry confirmation of a constituent recently isolated from the whole plant Isodon excisus is reported. An enantioselective catalytic boron-mediated reduction of an α-bromoketone was utilized in the key synthetic transformation. The methodology described herein was also used for the synthesis of the natural product's enantiomer and several derivatives. In addition, the compounds were evaluated for inhibitory activity in a caspase induction assay. The natural product was found to be devoid of activity, but several derivatives had moderate inhibitory activity (EC 50
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2003.10.025