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Published on: April 8, 2018
Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor
Yujiro Hayashi1, Mitsuru Shoji, Junichiro Yamaguchi
1Department of Industrial Chemistry, Faculty of Engineering, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. hayashi@ci.kagu.tus.ac.jp
Abstract:
The asymmetric total synthesis of (-)-azaspirene, an angiogenesis inhibitor, has been accomplished, establishing its absolute stereochemistry. The key steps are a MgBr2.OEt2-mediated, diastereoselective Mukaiyama aldol reaction, a NaH-promoted, intramolecular cyclization of an alkynylamide, and the aldol reaction of a ketone containing functionalized gamma-lactam moiety without protection of tert-alcohol and amide functionalities.
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