Synthesis of (+)-Febrifugine and a Formal Synthesis of (+)-Halofuginone Employing an Organocatalytic Direct Vinylogous Aldol Reaction

被引：14

作者：

Pansare, Sunil V. ^{[1
]}

Paul, Eldho K. ^{[1
]}

机构：

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

来源：

SYNTHESIS-STUTTGART | 2013年 / 45卷 / 13期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; aldol reaction; stereoselective synthesis; piperidines; total synthesis; CONCISE ENANTIOSELECTIVE SYNTHESIS; CATALYTIC ASYMMETRIC-SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; EFFICIENT SYNTHESIS; MICHAEL REACTION; FEBRIFUGINE; HALOFUGINONE; DERIVATIVES; ALDEHYDES; 2-(TRIMETHYLSILYLOXY)FURAN;

D O I：

10.1055/s-0033-1338706

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective organocatalytic direct vinylogous aldol reaction of gamma-crotonolactone and a suitable aldehyde was utilized in the synthesis of a functionalized gamma-butenolide. The gamma-butenolide (aldol product) was stereoselectively converted into a 5-aminoalkyl butyrolactone, which isomerized to the key 2,3-disubstituted piperidinone, a common intermediate to (+)-febrifugine and (+)-halofuginone.

引用

页码：1863 / 1869

页数：7

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