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Stereodivergent synthesis of 17-alpha and 17-beta-alpharyl steroids: application and biological evaluation of D-ring cortistatin analogues.

ABSTRACT: 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 alpha- and beta-configured D-ring aryl steroids. Biological evaluations of these "cortalogs" are reported for the first time.

SUBMITTER: Shi J

PROVIDER: S-EPMC3495592 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Stereodivergent synthesis of 17-alpha and 17-beta-alpharyl steroids: application and biological evaluation of D-ring cortistatin analogues.

Shi Jun J Shigehisa Hiroki H Guerrero Carlos A CA Shenvi Ryan A RA Li Chuang-Chuang CC Baran Phil S PS

Angewandte Chemie (International ed. in English) 20090101 24

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 alpha- and beta-configured D-ring aryl steroids. Biological evaluations of these "cortalogs" are reported for the first time. ...[more]

PMID: 19434636

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