Amino alcohols as potent organocatalysts in asymmetric aldol condensation: An enantioselective synthesis of Convolutamydine A

ORGN 291

Andrei V. Malkov, amalkov@chem.gla.ac.uk1, Marco Bella, Marco.Bella@uniroma1.it2, Mikhail A. Kabeshov1, Denis A. Malyshev1, Andrew Parkin3, and Pavel Kocovsky, P.Kocovsky@chem.gla.ac.uk1. (1) Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom, (2) Department of Chemistry, University of Rome “La Sapienza”, Piazzale Aldo Moro, 00185 Rome, Italy, (3) WestChem, Department of Chemistry, University of Glasgow, Glasgow, G12 8QQ, United Kingdom
Primary amino alcohols have been identified as efficient organocatalysts for an aldol condensation of activated ketones, such as isatin, with acetone and other sterically unhindered ketones. The aldol products, with a tertiary alcohol moiety, were formed in high enantiomeric purity (≤95% ee). Both enantiomers of marine alkaloid Convolutamydine A were synthesized for the first time in an enantiomerically pure form and the absolute configuration was confirmed by X-ray crystallography.
 

Total Synthesis of Complex Molecules
1:00 PM-4:40 PM, Monday, March 26, 2007 McCormick Place East -- Room E352, Level 3, Oral

Division of Organic Chemistry

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007