(+)-Rimocidin 合成研究：C(1-27)糖苷配基骨架的构建。
(+)-Rimocidin synthetic studies: construction of the C(1-27) aglycone skeleton.
机构信息
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
出版信息
J Org Chem. 2009 Aug 21;74(16):5987-6001. doi: 10.1021/jo900765p.
Abstract
Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the S(N)2/S(N)2' reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura cross-coupling completed construction of the C(1-27) rimocidinolide skeleton.
摘要
已通过收敛方式实现了 rimocidinolide（+)-rimocidin（1）的糖苷配基的 C(1-27) 大环骨架的组装。该合成策略的关键特点包括应用多组分 I 型阴离子接力化学 (ARC)，以及结合乙烯环氧化物的 S(N)2/S(N)2'反应流形，两者均采用 2-取代的 1,3-二噻烷来构建 C(1-19) 碳主链。通过 Yamaguchi 偶联，带有全反式三烯的 C(20-27) 乙烯基硼酸酯与先进的 C(1-19) 乙烯基碘化物结合，然后通过 Suzuki-Miyaura 交叉偶联进行大环化，完成了 C(1-27) rimocidinolide 骨架的构建。
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