Enantioselective approach to 7-azabicyclo[2.2.1]heptane ring systems using D-(-)-quinic acid as the chiral educt: Application to the formal synthesis of (+)-epibatidine

被引：28

作者：

Albertini, E ^{[1
]}

Barco, A ^{[1
]}

Benetti, S ^{[1
]}

DeRisi, C ^{[1
]}

Pollini, GP ^{[1
]}

Zanirato, V ^{[1
]}

机构：

[1] UNIV FERRARA,DIPARTMENTO CHIM,I-44100 FERRARA,ITALY

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 04期

关键词：

D O I：

10.1016/S0040-4039(96)02391-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By utilizing D-(-)-quinic acid as the chiral starting material die optically pure 7-[(1,1-dimethylethoxy)carbonyl]-7-azabicyclo[2.2.1.]heptan-2-one 2, an advanced intermediate already taken to (+)-epibatidine 1, a non-opioid analgesic isolated from Ecuadorian poison frogs, was synthetized through a facile, regioselective intramolecular nucleophilic ring opening of a cyclic sulfate moiety. (C) 1997, Elsevier Science Ltd.

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页码：681 / 684

页数：4

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