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
收藏
页码：10294 / 10298
页数：5
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