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Stereodivergent Synthesis of 17‐α and 17‐β‐Aryl Steroids: Application and Biological Evaluation of D‐Ring Cortistatin Analogues
Authors:Jun Shi  Hiroki Shigehisa Dr  Carlos A Guerrero  Ryan A Shenvi  Chuang‐Chuang Li Dr  Phil S Baran Prof
Institution:Department of Chemistry, The Scripps Research Institute, 10650 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1)?858‐784‐7375
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 α‐ and β‐configured D‐ring aryl steroids. Biological evaluations of these “cortalogs” are reported for the first time.
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Keywords:angiogenesis  asymmetric synthesis  natural products
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