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