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Concise Enantio‐ and Diastereoselective Total Syntheses of Fumagillol, RK‐805, FR65814, Ovalicin, and 5‐Demethylovalicin
Author(s) -
Yamaguchi Junichiro,
Toyoshima Maya,
Shoji Mitsuru,
Kakeya Hideaki,
Osada Hiroyuki,
Hayashi Yujiro
Publication year - 2006
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.200502826
Subject(s) - stereocenter , fumagillin , stereochemistry , chemistry , ring (chemistry) , total synthesis , cyclohexane , enantioselective synthesis , biology , organic chemistry , angiogenesis , cancer research , catalysis
L ‐Proline‐mediated α‐aminoxylation is a key step in the enantio‐ and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, and five or six contiguous stereogenic centers, and they display anti‐angiogenesis or immunosuppressive properties.