著者

高取 和彦 長澤 心 長岡 博人

出版者

日本薬学会化学系薬学部会

雑誌

反応と合成の進歩シンポジウム 発表要旨概要 第36回反応と合成の進歩シンポジウム

巻号頁・発行日

pp.153, 2010 (Released:2010-11-03)

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SmI2-induced cascade reaction involving reductive cyclization, Dieckmann condensation and lactonization has been developed in our laboratory, and applied to the total synthesis of (+-)-gibberellin A1. Herein, we report the further application of the reaction to the synthesis of antheridiogen-An, isolated from Anemia phyllitidis in 1971 by Nakanishi and coworkers, having unique tetracycic ring system with gamma-lactone. Our synthetic features for the challenging synthetic target were shown as follows. The CD ring was formed by SmI2-induced fragmentation reaction of the cyclopropane ring in the tricyclo[3.2.1.02,7]octane derivative, prepared by Michael-Michael-alkylation reaction. Formation of functionalized antheridane skeleton as a key step was achieved by application of the SmI2-induced reductive cyclization-Dieckmann condensation-lactonization of the keto diester as a intermediate.