Abstract

Chiral non-racemic 4-substituted 3,5-diacyl-1,4-dihydropyridines 8 are prepared by the regio- and diastereoselective addition of organocopper reagents to chiral pyridinium salt 2, followed by acylation with trichloroacetic anhydride and subsequent haloform reaction. Additionally, (−)- N a -methylervitsine is synthesized by reaction of the enolate derived from 2-acetylindole 9 with pyridinium salt 2, followed by electrophile (Me 2N +CH 2I −)-induced cyclization and subsequent elaboration of the 16-methylene and (20 E)-ethylidene substituents.

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