N-methoxy-N-acylnitrenium ions: application to the formal synthesis of (-)-TAN1251A.
[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.
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. wardropd@uic.edu
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D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D007477:Ions / Q000737:chemistry*; D015394:Molecular Structure; D018727:Muscarinic Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D014443:Tyrosine / Q000737:chemistry*
D001372:Aza Compounds; D007477:Ions; D018727:Muscarinic Antagonists; D013141:Spiro Compounds; C429313:TAN1251A; D014443:Tyrosine