The Total Synthesis of (-)-7-Deoxyloganin via N-Heterocyclic Carbene Catalyzed Rearrangement of α,β-Unsaturated Enol Esters

被引：97

作者：

Candish, Lisa ^{[1
]}

Lupton, David W. ^{[1
]}

机构：

[1] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 21期

关键词：

DIELS-ALDER REACTIONS; NATURALLY-OCCURRING IRIDOIDS; DIASTEREOSELECTIVE CONJUGATE ADDITION; ASYMMETRIC TOTAL-SYNTHESIS; WITTIG-HORNER REACTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GRIGNARD-REAGENTS; MICHAEL REACTIONS; SECOIRIDOIDS;

D O I：

10.1021/ol101983h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

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页码：4836 / 4839

页数：4

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