Regioselective synthesis of bridged azabicyclic compounds using radical translocations/cyclisations of methyl 2-alkynyl-1-(o-iodobenzoyl)pyrrolidine-2-carboxylates: a formal total synthesis of (+/-)-epibatidine

被引：29
作者：
Ikeda, M
Kugo, Y
Kondo, Y
Yamazaki, T
Sato, T
机构：
[1] Kyoto Pharmaceutical University, Misasagi, Yamashina
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 22期
关键词：
D O I：
10.1039/a705226j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bu3SnH-mediated radical translocations/cyclisations of methyl 2-alkynyl-1-(o-iodobenzoyl)pyrrolidine-2-carboxylates have been examined, The 2-[3-(trimethylsilyl)prop-2-ynyl]-8,2-[4-(trimethylsilyl)but-3- ynyl]-14, and 2-[5-(trimethylsilyl)pent-4-ynyl]-pyrrolidine derivatives 18, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave, regioselectively, the 7-azabicyclo-[2,2,1]heptane 19, 8-azabicyclo[3.2.1]octane 23, and 9-azabicyclo[4.2.1]nonane 26, respectively, The method has been applied to a formal total synthesis of (+/-)-epibatidine.
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页码：3339 / 3344
页数：6
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