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A divergent enantioselective approach to hapalindole-type alkaloids is described. The route features a ruthenium-catalyzed asymmetric hydrogenation of a ketone via DKR to construct the chiral trans -1-indolyl-2-isopropenylcyclohexane skeleton and a switchable sequence of methylation and acetylation/aldol reaction to access a chiral quaternary stereocenter. (+)-Hapalindole Q ( 1 , 13 steps, 5.9% overall yield), (-)- 12 - epi -hapalindole Q isonitrile ( 2 , 15 steps, 5.5% overall yield), (-)-hapalindole D ( 3 , 14 steps, 2.3% overall yield), and (+)- 12 - epi -fischerindole U isothiocyanate ( 4 , 14 steps, 3.0% overall yield) were synthesized in 13-15 steps from a commercially available material to demonstrate the application of this approach.

chemical science

Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure