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Asymmetric Total Synthesis of (−)-Azaspirene, a Novel Angiogenesis Inhibitor
datasetposted on 18.09.2002, 00:00 by Yujiro Hayashi, Mitsuru Shoji, Junichiro Yamaguchi, Kenji Sato, Shinpei Yamaguchi, Takasuke Mukaiyama, Ken Sakai, Yukihiro Asami, Hideaki Kakeya, Hiroyuki Osada
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 γ-lactam moiety without protection of tert-alcohol and amide functionalities.