硅烷基添加剂中抑制差向异构化的普林斯环化反应：天然产物四氢吡喃骨架合成中的通用工具。
Prins cyclizations in silyl additives with suppression of epimerization: versatile tool in the synthesis of the tetrahydropyran backbone of natural products.
作者信息
Chan Kok-Ping, Loh Teck-Peng
机构信息
Divison of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore 637616.
出版信息
Org Lett. 2005 Sep 29;7(20):4491-4. doi: 10.1021/ol051951q.
PMID:16178566
Abstract
[reactions: see text] A catalytic Prins cyclization reaction has been developed. The involvement of trimethylsilyl halides offers a versatile route to the formation of cis-4-halo-2,6-disubstituted tetrahydropyran rings. The problem of epimerization in Prins cyclization has also been addressed in the total synthesis of (-)-centrolobine using this methodology.
摘要
[反应：见正文] 已开发出一种催化普林斯环化反应。三甲基硅基卤化物的参与为顺式-4-卤代-2,6-二取代四氢吡喃环的形成提供了一条通用途径。在使用该方法全合成（-）-中心洛宾时，也解决了普林斯环化中的差向异构化问题。
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