Abstract
Abstract The total synthesis of (±)-TAN1251A possessing an antimuscarinic activity was achieved. Carboxylic acid ( 1 ) was converted into carbamate ( 3 ) through a sequence of alkylation and Curtius rearrangement. After a few functional group interconversions of 3 , the corresponding amine ( 9 ) was converted into an azaspiro molecule ( 18 ) through cyclization and installation of a C 2 unit. Hydrolysis of 18 followed by lactam formation afforded tricyclic compound ( 20 ). Coupling of 20 with aldehyde ( 22 ) gave two epimeric adducts, ( 23A ) and ( 23B ), which were converted into TAN1251A by four steps.
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