A Modular Approach to the Asymmetric Synthesis of Cytisine

被引：21

作者：

Struth, Felix R. ^{[1
]}

Hirschhaeuser, Christoph ^{[1
]}

机构：

[1] Univ Duisburg Essen, Inst Organ Chem, Univ Str 7, D-45141 Essen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 05期

关键词：

Asymmetric synthesis; Natural products; Alkaloids; Metathesis; Rearrangement; Carbenoids; Boronate homologation; NICOTINIC ACETYLCHOLINE-RECEPTORS; PINANEDIOL BORONIC ESTERS; SMOKING-CESSATION; CRYSTAL-STRUCTURE; DIASTEREOSELECTIVE FUNCTIONALIZATION; BINDING PROTEIN; PARTIAL AGONIST; (-)-CYTISINE; DERIVATIVES; (+/-)-CYTISINE;

D O I：

10.1002/ejoc.201501435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of (+)- and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.

引用

页码：958 / 964

页数：7

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