Stereoselective approach to C-aryl pyranoside synthesis which addresses the problem of C7-substitution in blepharocalyxin E
Stereoselective approach to C-aryl pyranoside synthesis which addresses the problem of C7-substitution in blepharocalyxin E
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DOI：
10.1021/jo0355909
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发表时间：
2004-03-19
影响因子：
3.6
通讯作者：
Mead, KT
中科院分区：
文献类型：
--
作者：
Cakir, SP;Mead, KT
开发了一系列芳基取代的吡喃糖苷衍生物的一般路线，作为合成睑萼素E的模型。制备了两种外取代的四氢-4H-呋喃并[2,3-b]吡喃-2-酮衍生物8a和8b，并在路易斯酸条件下分别用苯甲醚和苯氧基三异丙基硅烷处理，以实现C-芳基吡喃糖苷的合成。在每种情况下，都会形成γ-内酯，并在酸处理时重新排列成所需的结构。通过该路线以单一异构体形式制备了四种化合物（12、14、16 和 18），总产率良好。
A general route to a series of aryl- substituted pyranoside derivatives has been developed as a model for the synthesis of blepharocalyxin E. Two exo-substituted tetrahydro-4H-furo[2,3-b]pyran-2-one derivatives, 8a and 8b, were prepared and treated separately with anisole and phenoxytriisopropylsilane under Lewis acid conditions to effect C-aryl pyranoside synthesis. In each case, a gamma-lactone was formed, which rearranged to the desired structure on acid treatment. Four compounds (12, 14, 16, and 18) were prepared by this route as single isomers in good overall yield.