Synthesis of the quinolizidine alkaloids (-)-lasubine II and (±)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones

被引：53

作者：

Back, TG ^{[1
]}

Hamilton, MD ^{[1
]}

Lim, VJJ ^{[1
]}

Parvez, M ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 03期

关键词：

D O I：

10.1021/jo048284j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate additions of (2-piperidyl)acetate esters to acetylenic sulfones, followed by LDA-promoted intramolecular acylations, afforded cyclic enaminones that were readily converted into the corresponding 4-substituted 2-keto- or 2-hydroxyquinolizidines by stereoselective reduction and desulfonylation. This procedure was applied to the total synthesis of (-)-lasubine II from methyl (S)-(2-piperidyl)acetate and 2-(3,4-dimethoxyphenyl)-1-(p-toluenesulfonyl)ethyne. Similarly, methyl (+/-)-(2-piperidyl)acetate and 1-(p-toluenesulfonyl)propyne provided (+/-)-myrtine.

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页码：967 / 972

页数：6

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