Toward Pyridine-Heterocycle Patterns through Prins and Aza-Prins Cyclisations: Application to a Short Synthesis of (±)-Anabasine

被引：12

作者：

Colin, Olivier ^{[1
]}

Greck, Christine ^{[1
]}

Prim, Damien ^{[1
]}

Thomassigny, Christine ^{[1
]}

机构：

[1] Univ Versailles St Quentin en Yvelines, ILV UMR CNRS 8180, F-78035 Versailles, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 31期

关键词：

Nitrogen heterocycles; Oxygen heterocycles; Natural products; Cyclization; Hydrogenation; Prins reaction; MOLECULAR-STRUCTURE; PALLADIUM; ACID; HYDROFORMYLATION; CONFIGURATION; COMPLEXATION; RESOLUTION; POTENT;

D O I：

10.1002/ejoc.201402971

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The formation of pyridine-containing bisheterocycles through a Prins-type cyclisation is described. Pyridine-tetrahydropyran and pyridine-piperidine conjugates could be efficiently obtained using various carbaldehydes including dicarbaldehydes, and either homoallylic alcohols or a homoallylic amine. Selective partial or complete hydrogenation led to new bisheterocycle combinations. A two-step sequence involving an aza-Prins cylisation allowed us to prepare the alkaloid anabasine.

引用

页码：7000 / 7005

页数：6

共 4 条

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