Catalytic asymmetric total syntheses of quinine and quinidine.
The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.
Raheem
Izzat T
IT
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.
Goodman
Steven N
SN
Jacobsen
Eric N
EN
D002384:Catalysis; D011802:Quinidine / Q000138:chemical synthesis*; D011803:Quinine / Q000138:chemical synthesis*; D013237:Stereoisomerism
D011803:Quinine; D011802:Quinidine