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

Citation
Dj. Wardrop et A. Basak, N-methoxy-N-acylnitrenium ions: Application to the formal synthesis of (-)-TAN1251A, ORG LETT, 3(7), 2001, pp. 1053-1056
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
7
Year of publication
2001
Pages
1053 - 1056
Database
ISI
SICI code
1523-7060(20010405)3:7<1053:NIATTF>2.0.ZU;2-Y
Abstract
[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 const ruction of the 1-azaspiro[4.5]decane skeleton present in the natural produc t by an N-methoxy-N-acylnitrenium ion-induced spirocyclization. The dienone generated in this transformation, 10, was converted to (-)-TAN1251A via tr icycle 9, an intermediate in Kawahara's recent synthesis of racemic 7.