SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES
SYNTHESIS OF THE NOVEL ANTILEUKEMIC TETRAHYDROCYCLOPENTA[B]BENZOFURAN, ROCAGLAMIDE AND RELATED SYNTHETIC STUDIES
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DOI：
10.1039/p19920002657
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发表时间：
1992-10-21
期刊：
影响因子：
--
通讯作者：
TAYLOR, RJK
中科院分区：
文献类型：
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作者：
DAVEY, AE;SCHAEFFER, MJ;TAYLOR, RJK
两种方法的罗格列胺三环骨架进行了说明。第一，它采用了一个不寻常的分子内二噻烷基阴离子羰基加成反应，提供了获得α-苯基rocaglamide类似物。第二条路线涉及分子内酮醛频哪醇偶联的关键步骤，并可用于制备一系列具有α-和β-苯基取代基的罗格列胺类似物。使用第二种方法描述了外消旋形式的罗格列胺的全合成。该合成路线从间苯三酚开始，间苯三酚是一种廉价且容易获得的起始材料，并且仅需要8/9个步骤，总收率> 6%。还描述了1 -表-罗格列酰胺29 b的合成。
Two approaches to the rocaglamide tricyclic skeleton are described. The first, which employs an unusual intramolecular dithianyl anion to carbonyl addition reaction, provides access to alpha-phenyl rocaglamide analogues. The second route involves an intramolecular keto aldehyde pinacolic coupling in the key step and can be used for the preparation of a whole range of rocaglamide analogues possessing both alpha- and beta-phenyl substituents. A total synthesis of rocaglamide, in racemic form, is described using this second approach. The synthetic route commences with phloroglucinol, an inexpensive and readily-available starting material, and takes only 8/9 steps giving an overall yield of >6%. The synthesis of 1 -epi-rocaglamide 29b is also described.