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.
引用
收藏
页码：4836 / 4839
页数：4
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