利用二碘化钐促进的8-内型酮基-烯烃环化反应全合成(+)-异五味子素
Total synthesis of (+)-isoschizandrin utilizing a samarium(II) iodide-promoted 8-endo ketyl-olefin cyclization.
作者信息
Molander Gary A, George Kelly M, Monovich Lauren G
机构信息
Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA.
出版信息
J Org Chem. 2003 Dec 12;68(25):9533-40. doi: 10.1021/jo0347361.
The 13-step synthesis of (+)-isoschizandrin reported herein features a samarium(II) iodide-promoted 8-endo ketyl-olefin coupling to assemble the eight-membered ring present in the target concomitantly with the required functionality and stereochemistry. In constructing (+)-isoschizandrin as a single atropisomer, the synthesis utilizes a kinetic resolution of a seven-membered lactone using a CBS-oxazaborolidine.
本文报道的（+）-五味子醇甲的13步合成以碘化钐（II）促进的8-内型酮基-烯烃偶联为特色，用于构建目标化合物中存在的八元环，并同时引入所需的官能团和立体化学。在将（+）-五味子醇甲构建为单一阻转异构体时，该合成利用了CBS-恶唑硼烷对七元内酯进行动力学拆分。
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