Total syntheses of enantiomerically enriched R-(+)-and S-(−)-deplancheine

N Sydorenko, CA Zificsak, AI Gerasyuto…

Index: Sydorenko, Nadiya; Zificsak, Craig A.; Gerasyuto, Aleksey I.; Hsung, Richard P. Organic and Biomolecular Chemistry, 2005 , vol. 3, # 11 p. 2140 - 2144

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Citation Number: 34

Abstract

Total syntheses of indoloquinolizidine alkaloid (±)-, R-(+)-, and S-(−)-deplancheine are described here. The synthesis features an enantioselective intramolecular formal aza-[3+ 3] cycloaddition for the construction of the quinolizidine CD-ring. This application serves to introduce a new synthetic strategy for the synthesis of indoloquinolizidine alkaloids.