Total Synthesis of (+)- and (−)-Calycanthine by Means of Thio-Urea-Catalyzed Sequential Michael Reactions of Bis-oxindoles

A unified catalytic asymmetric approach to naturally occurring piperidinoindoline and pyrrololidinoindoline alkaloids has been realized via the development of a thio-urea-catalyzed sequential Michael addition of bis-oxindole onto nitroethylene (up to 93% ee and >20:1 dr). This strategy offers the total syntheses of either enantiomers of naturally occurring calycanthine.