Catalytic Asymmetric Total Syntheses of Quinine and Quinidine

Izzat T. Raheem, Steven N. Goodman, and Eric N. Jacobsen*
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138
J. Am. Chem. Soc., 2004, 126 (3), pp 706–707
DOI: 10.1021/ja039550y
Publication Date (Web): December 31, 2003
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, jacobsen@chemistry.harvard.edu

Abstract

Abstract Image

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.

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History

  • Published In Issue January 28, 2004
  • Received November 11, 2003

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