Synthesis of (-)-Cytisine Using a 6-endo aza-Michael Addition

被引：17

作者：

Barat, Viktor ^{[1
]}

Csokas, Daniel ^{[1
]}

Bates, Roderick W. ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 16期

关键词：

ENANTIOSELECTIVE SYNTHESIS; DERIVATIVES; ALKALOIDS; CYTISINE; ROUTE;

D O I：

10.1021/acs.joc.8b01156

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An asymmetric synthesis of (-)-cytisine has been achieved. The piperidine C-ring was formed using a stereodivergent intramolecular 6-endo aza-Michael addition. The B-ring was established by intramolecular pyridine N-alkylation. The absolute stereochemistry was established by an Evans acyl oxazolidinone enolate alkylation reaction that proceeded with an unexpected stereochemical outcome due to participation of the pyridine nitrogen lone pair.

引用

页码：9088 / 9095

页数：8

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