De Novo Asymmetric Synthesis of an α-6-Deoxyaltropyranoside as Well as its 2-/3-Deoxy and 2,3-Dideoxy Congeners
De Novo Asymmetric Synthesis of an α-6-Deoxyaltropyranoside as Well as its 2-/3-Deoxy and 2,3-Dideoxy Congeners
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DOI：
10.1021/jo9009722
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发表时间：
2009-08-21
影响因子：
3.6
通讯作者：
O'Doherty, George A.
中科院分区：
文献类型：
--
作者：
Shan, Mingde;Xing, Yalan;O'Doherty, George A.
通过一种常见的吡喃酮中间体，实现了苄基α -6-脱氧乙酰吡喃苷、苄基α -天门冬旋吡喃苷、苄基α -氨基吡喃苷和苄基A -地丁氧吡喃苷的高度分散的新不对称合成。该路线依赖于钯(0)催化的糖基化反应和相应的糖基化后转化，绝对和相对立体构型的控制来自于2-酰基呋喃的Noyori还原和随后的非对映选择性引入其他立体中心。
A highly divergent de novo asymmetric synthesis of benzyl alpha-6-deoxyaltropyranoside, benzyl alpha-ascarylopyranoside, benzyl alpha-amicetopyranoside, and benzyl a-digitoxopyranoside has been achieved via I common pyranone intermediate. The routes rely upon it palladium(0)-catalyzed glycosylation reaction and corresponding post-glycosylation transformations, The control of the absolute and relative stereochemical configuration came from a Noyori reduction of 2-acylfuran and subsequent diastereoselective introduction of other stereogenic centers.