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Asymmetric Total Synthesis of (−)-Azaspirene, a Novel Angiogenesis Inhibitor

2002; American Chemical Society; Volume: 124; Issue: 41 Linguagem: Inglês

10.1021/ja0276826

1943-2984

Yujiro Hayashi, Mitsuru Shoji, Junichiro Yamaguchi, Kenji Sato, Shinpei Yamaguchi, T. MUKAIYAMA, Ken Sakai, Yukihiro Asami, Hideaki Kakeya, Hiroyuki Osada,

Marine Sponges and Natural Products

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.