从d-葡萄糖和d-甘露糖衍生的多取代1,6-二烯的tosyl自由基介导环化的立体诱导

Dora-Marina Gutierrez-Avella, Michèle Bertrand, Robert Nouguier
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引用次数: 0

摘要

多取代的1,6-二烯1和6是由6-碘-d-甘露糖苷和d- glucopyrano苷通过bod裂解和随后的烯烃得到的,在自由基条件下加入TsSePh后发生环化。功能化环戊醇是由氢化三丁基锡介导的加合物还原而产生的。对立体感应进行了初步的合理化,并与文献中的相关数据进行了比较。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Stereoinduction in the tosyl radical-mediated cyclization of polysubstituted 1,6-dienes derived from d-glucose and d-mannose

Polysubstituted 1,6-dienes 1 and 6, derived from 6-iodo-d-manno- and d-glucopyranosides through Boord fragmentation and subsequent olefination, undergo cyclization upon addition of TsSePh under radical conditions. Functionalized cyclopentitols result from tributyltin hydride mediated reduction of the adducts. A tentative rationalization of steroinduction is given, and a comparison is made with related data in the literature.

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