Total syntheses of enantiomerically enriched R-(+)- and S-(-)-deplancheine.
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.
Sydorenko
Nadiya
N
Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.
Zificsak
Craig A
CA
Gerasyuto
Aleksey I
AI
Hsung
Richard P
RP
D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013237:Stereoisomerism
D026121:Indole Alkaloids; C496494:deplancheine