N-Methoxy-N-acylnitrenium Ions: Application to the Formal Synthesis of (−)-TAN1251A
- 14 March 2001
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 3 (7) , 1053-1056
- https://doi.org/10.1021/ol015626o
Abstract
[structure: see text]. 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.Keywords
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