Organocatalytic enantioselective synthesis of 1,3,5-polyols by means of iterative asymmetric epoxidation: their application to the total synthesis of polyrhacitide A

被引：13

作者：

Kumaraswamy, Gullapalli ^{[1
]}

Murthy, Akula Narayana ^{[1
,2
]}

Sadaiah, Kadivendi ^{[1
]}

机构：

[1] Indian Inst Chem Technol, Organ Div 3, Hyderabad 500607, Andhra Pradesh, India

[2] Univ Hyderabad, Associate Inst, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON | 2012年 / 68卷 / 15期

关键词：

STEREOSELECTIVE TOTAL-SYNTHESIS; CHINESE MEDICINAL ANTS; FORMAL TOTAL-SYNTHESIS; TRANSFER HYDROGENATION; CARBONYL ALLYLATION; ALDOL REACTIONS; CONSTRUCTION; 1,3-POLYOLS; STRATEGY; ACCESS;

D O I：

10.1016/j.tet.2012.02.055

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed a pragmatic route to the stereogenic skipped 1,3,5-polyols. The strategic transformation includes an organocatalytic enantioselective asymmetric epoxidation, which is either syn- or anti-selective as genesis of chirality and successive S(N)2 opening reaction by an appropriate functionalized nucleophile, followed by hydroboration/oxidation to generate stereoisomers in good yield. The critical intermediate generated en route to this process is employed in the total synthesis of polyrhacitide A. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：3179 / 3186

页数：8

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