Total synthesis of (10R)- and (10S)-corossolin: Determination of the stereochemistry at C-10 of the natural corossolin and the differential toxicity toward cancer cells caused by the configuration at C-10

Citation
Q. Yu et al., Total synthesis of (10R)- and (10S)-corossolin: Determination of the stereochemistry at C-10 of the natural corossolin and the differential toxicity toward cancer cells caused by the configuration at C-10, J ORG CHEM, 64(7), 1999, pp. 2440-2445
Citations number
16
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
0022-3263 → ACNP
Volume
64
Issue
7
Year of publication
1999
Pages
2440 - 2445
Database
ISI
SICI code
0022-3263(19990402)64:7<2440:TSO(A(>2.0.ZU;2-Y
Abstract
(10R) and (10S)-corossolin have been synthesized by coupling of the alkyne intermediate 18 with epoxide 27 or 29, respectively. Comparison of the phys ical data of both synthetic corossolins with those reported for the natural one shows that the configuration at C-10 of the natural corossolin is high ly likely to be R. The R isomer is found to be 18 times as active as the S isomer in the preliminary in vitro tests against the B16BL6 cell line.