Total synthesis of (-)-centrolobine:: β-C-glycoside formation via a tandem Grignard addition and stereoselective hemi-ketal reduction

被引：56

作者：

Jennings, MP ^{[1
]}

Clemens, RT ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 12期

关键词：

C-glycoside; centrolobine; ring-closing metathesis; one-pot reaction; tetrahydropyran;

D O I：

10.1016/j.tetlet.2005.01.156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been demonstrated that an aryl-beta-Gglycoside can be efficiently constructed via a sequence consisting of Brown asymmetric allylation, ring-closing metathesis, hydrogenation, nucleophilic addition, and stereoselective Et3SiH reduction. The antibiotic natural product (-)-centrolobine was synthesized in this manner utilizing only five steps with an overall 53% yield. (C) 2005 Elsevier Ltd. All rights reserved.

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页码：2021 / 2024

页数：4

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