N-methoxy-N-acylnitrenium ions:: Application to the formal synthesis of (-)-TAN1251A

被引：106

作者：

Wardrop, DJ ^{[1
]}

Basak, A ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 07期

关键词：

D O I：

10.1021/ol015626o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A formal synthesis of the muscarinic M-1 receptor antagonist (-)-TAN1251A (7) from L-tyrosine is described. Central to this venture has been the construction of the 1-azaspiro[4.5]decane skeleton present in the natural product by an N-methoxy-N-acylnitrenium ion-induced spirocyclization. The dienone generated in this transformation, 10, was converted to (-)-TAN1251A via tricycle 9, an intermediate in Kawahara's recent synthesis of racemic 7.

引用

页码：1053 / 1056

页数：4

共 39 条

[31] DIPHENYLPHOSPHORYL AZIDE - NEW CONVENIENT REAGENT FOR A MODIFIED CURTIUS REACTION AND FOR PEPTIDE SYNTHESIS [J].