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

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Yujiro Hayashi,*^† Mitsuru Shoji,^† Junichiro Yamaguchi,^† Kenji Sato,^† Shinpei Yamaguchi,^† Takasuke Mukaiyama,^† Ken Sakai,^§ Yukihiro Asami, Hideaki Kakeya, and Hiroyuki Osada

Department of Industrial Chemistry, Faculty of Engineering, and Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan, and Antibiotics Laboratory, RIKEN, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan

J. Am. Chem. Soc., 2002, 124 (41), pp 12078–12079

DOI: 10.1021/ja0276826

Publication Date (Web): September 18, 2002

To whom correspondence should be addressed. E-mail: hayashi@ ci.kagu.tus.ac.jp.

†

Department of Industrial Chemistry, Faculty of Engineering, Tokyo University of Science.

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science.

Antibiotics Laboratory, RIKEN.

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 γ-lactam moiety without protection of tert-alcohol and amide functionalities.

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Published In Issue October 16, 2002
Received July 12, 2002

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Communication

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

Abstract

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History

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Related Content

Asymmetric Total Synthesis of Pseurotin A

First Asymmetric Total Synthesis of Synerazol, an Antifungal Antibiotic, and Determination of Its Absolute Stereochemistry

Total Synthesis of (−)-Penifulvin A, an Insecticide with a Dioxafenestrane Skeleton

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