The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters
The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters
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DOI：
10.1021/ol101983h
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发表时间：
2010-11-05
期刊：
影响因子：
5.2
通讯作者：
Lupton, David W.
中科院分区：
文献类型：
--
作者：
Candish, Lisa;Lupton, David W.
α，β-不饱和烯醇酯（S）-2b的非对映选择性N-杂环卡宾（NHC）催化的重排已用于组装二氢吡喃酮（S）-3b，二氢吡喃酮（S）-3b是体现环烯醚萜类天然产物家族的双环核心的材料。通过化学选择性还原和随后的立体选择性β-糖基化，对该中间体进行酯化，使得（-）-7-脱氧马钱苷（1）的全合成在四个后续步骤中实现。
The diastereoselective N-heterocyclic carbene (NHC) catalyzed rearrangement of alpha,beta-unsaturated enol ester (S)-2b has been used to assemble dihydropyranone (S)-3b, a material embodying the bicyclic core of the iridoid family of natural products. Elaboration of this intermediate, by chemoselective reduction followed by stereoselective beta-glycosylation, has allowed the total synthesis of (-)-7-deoxyloganin (1) to be achieved in four subsequent steps.