用于构建与柯蒲木碱生物碱相关的六环骨架的环加成方法。
Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids.
作者信息
Hong Xuechuan, France Stefan, Mejía-Oneto José M, Padwa Albert
机构信息
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
出版信息
Org Lett. 2006 Oct 26;8(22):5141-4. doi: 10.1021/ol062029z.
Abstract
An approach to the hexacyclic framework of the kopsifoline alkaloids has been developed and is based on a Rh(II)-catalyzed cyclization-cycloaddition cascade. The resulting [3+2]-cycloadduct was readily converted into the TBS enol ether 23. Oxidation of the primary alcohol present in 23 followed by reaction with CsF afforded compound 24 that contains the complete hexacyclic skeleton of the kopsifolines. [reaction: see text]
摘要
已经开发出一种构建柯蒲木碱六环骨架的方法，该方法基于铑（II）催化的环化-环加成串联反应。所得的[3+2]环加成产物很容易转化为叔丁基二甲基硅烷基（TBS）烯醇醚23。对23中存在的伯醇进行氧化，然后与氟化铯反应，得到含有柯蒲木碱完整六环骨架的化合物24。[反应：见原文]
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