Synthesis of (+)-Ipalbidine Based on 6-exo-trig Radical Cyclization of a β-Amino Radical

被引：3

作者：

Chea, JongMyoung ^{[1
]}

Clive, Derrick L. J. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

RING-CLOSURE; PYRROLIDINES; INDOLIZIDINE; IPALBIDINE; ALLENES; ROUTE; GENERATION; KINETICS; OLEFINS; SYSTEM;

D O I：

10.1021/acs.joc.5b01890

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Boc (S)-proline was converted into (2S)-2-[(phenylselanyl)methyl]pyrrolidine, which was alkylated on nitrogen with 2-bromo-1-(4-methoxyphenyl)ethan-1-one. Reaction with vinyl-lithium, 6-exo-trig radical cyclization (Bu3SnH, AIBN, PhMe, 110 degrees C), dehydration (P2O5, H3PO4), and demethylation (BBr3) gave (+)-ipalbidine with ee >99%.

引用

页码：10294 / 10298

页数：5

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