Journal
ORGANIC LETTERS
Volume 3, Issue 7, Pages 1053-1056Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol015626o
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- NIGMS NIH HHS [GM59157-01] Funding Source: Medline
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[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.
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