Shiina Isamu, Takasuna Yu-Ji, Suzuki Ryo-Suke, Oshiumi Hiromi, Komiyama Yuri, Hitomi Seiichi, Fukui Hiroki
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan.
Org Lett. 2006 Nov 9;8(23):5279-82. doi: 10.1021/ol062058+.
[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.
[结构:见正文] 通过几种特色合成方法实现了伪2-表博落回醇内酯(1b)的全合成。首先,通过不对称羟醛反应立体选择性地构建九元环化合物的手性线性前体,以制备β-羟基酯单元。其次,通过由2-甲基-6-硝基苯甲酸酐(MNBA)与碱性促进剂促进的极其简便且有效的混合酸酐方法,高效地实现了形成九元内酯部分的关键环化反应。