Stereoselective total synthesis of the proposed structure of 2-epibotcinolide.

Isamu Shiina, Yu-Ji Takasuna, Ryo-Suke Suzuki, Hiromi Oshiumi, Yuri Komiyama, Seiichi Hitomi, Hiroki Fukui

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan. shiina@ch.kagu.tus.ac.jp

Organic letters 2006 Nov 9

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Structure: see text] The total synthesis of pseudo 2-epibotcinolide (1b) through several featured synthetic approaches has been attained. First, the chiral linear precursors of the nine-membered ring compound is stereoselectively constructed by the asymmetric aldol reaction for producing beta-hydroxy ester units. Second, the key cyclization reaction to form the nine-membered lactone moiety is efficiently achieved by the extremely facile and powerful mixed-anhydride method promoted by 2-methyl-6-nitrobenzoic anhydride (MNBA) with basic promoters.

Citation

Isamu Shiina, Yu-Ji Takasuna, Ryo-Suke Suzuki, Hiromi Oshiumi, Yuri Komiyama, Seiichi Hitomi, Hiroki Fukui. Stereoselective total synthesis of the proposed structure of 2-epibotcinolide. Organic letters. 2006 Nov 9;8(23):5279-82