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Catalytic Asymmetric Total Syntheses of Quinine and Quinidine
Raheem, Izzat T.,Goodman, Steven N.,Jacobsen, Eric N.
, p. 706 - 707 (2007/10/03)
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. Copyright
