A Simple Enantioselective Route to Functionalized Indolizidines: Synthesis of (+)-Ipalbidine and (+)-Antofine

被引：26

作者：

Pansare, Sunil V. ^{[1
]}

Lingampally, Rajinikanth ^{[1
]}

Dyapa, Rajendar ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 12期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

Organocatalysis; Michael addition; Alkaloids; Ipalbidine; Antofine; ORGANOCATALYTIC MICHAEL ADDITION; ASYMMETRIC TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; TYLOPHORA ALKALOIDS; BIOLOGICAL-ACTIVITY; CONJUGATE ADDITION; FORMAL SYNTHESIS; AMINO-ACIDS; PHENANTHROINDOLIZIDINE; KETONES;

D O I：

10.1002/ejoc.201100125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient route to functionalized indolizidines from an enantiomerically enriched gamma-nitro ketone is described. The nitro ketone is obtained by an organocatalytic, enantioselective ketone-nitro alkene Michael addition. Oxidative ring expansion of the nitro ketone and subsequent methanolysis provides a 8-nitro-4-oxooctanoate. This is stereoselectively transformed to the key, functionalized indolizidine intermediate which is readily converted to (+)-ipalbidine and (+)-antofine.

引用

页码：2235 / 2238

页数：4

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