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Paper | Regular issue | Vol 53, No. 5, 2000, pp.1051-1064
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8839
Formal Total Synthesis of Aglaiastatin: Pd(0)-mediated Construction of Benzofurocyclopentane System

Takumi Watanabe, Yuichiro Shiraga, Tomio Takeuchi, Masami Otsuka, and Kazuo Umezawa*

*Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-0061, Japan

Abstract

Aglaiastatin, an antitumor alkaloid, contains fused pentacyclic system, including a benzofurocyclopentane system and a unique pyrrolopyrimidinone skeleton. In this study, synthesis of a keto aldehyde intermediate, a key intermediate in a previously reported procedure for total synthesis, was accomplished via Pd(0)-mediated benzofuran ring closure. Thus, a formal total synthesis of aglaiastatin was achieved.