HETEROCYCLES

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■ Studies toward the Synthesis of Perforatumone: Synthesis of the 7-Oxabicyclo[4.2.1]nonane-8,9-dione Core

Tatsuki Nakajima, Keita Takiguchi, Keisuke Yoshida, Akihiro Ogura, and Ken-ichi Takao*

*Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan

Abstract

Construction of the unique bridged bicyclic skeleton, 7-oxabicyclo[4.2.1]nonane-8,9-dione, of perforatumone was achieved. Key steps included a Dieckmann-type condensation, a Claisen rearrangement, and an intramolecular Michael reaction.