Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids
Cycloaddition protocol for the assembly of the hexacyclic framework associated with the kopsifoline alkaloids
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DOI：
10.1021/ol062029z
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发表时间：
2006-10-26
期刊：
影响因子：
5.2
通讯作者：
Padwa, Albert
中科院分区：
文献类型：
--
作者：
Hong, Xuechuan;France, Stefan;Padwa, Albert
已开发的kopsifoline生物碱的六环框架的方法，是基于铑（II）催化的环化-环加成级联。所得的[3+2]-环加合物容易地转化成TBS烯醇醚23。将存在于23中的伯醇氧化，然后与CsF反应，得到含有kopsifolines的完整六环骨架的化合物24。
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.