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Stereodivergent Synthesis of 17‐α and 17‐β‐Aryl Steroids: Application and Biological Evaluation of D‐Ring Cortistatin Analogues
Author(s) -
Shi Jun,
Shigehisa Hiroki,
Guerrero Carlos A.,
Shenvi Ryan A.,
Li ChuangChuang,
Baran Phil S.
Publication year - 2009
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.200901116
Subject(s) - stereocenter , ring (chemistry) , stereochemistry , aryl , chemistry , combinatorial chemistry , biochemistry , enantioselective synthesis , organic chemistry , alkyl , catalysis
One stereocenter makes all the difference : The synthesis and biological evaluation of 17‐ epi ‐cortistatin A is reported from a common intermediate used to procure natural cortistatin A. The synthesis features a unique stereocontrolled Raney‐Ni reduction process that can be employed to reliably produce both α‐ and β‐configured D‐ring aryl steroids. Biological evaluations of these “cortalogs” are reported for the first time.