Synthesis of (−)-Stemoamide Using a Stereoselective anti-Aldol Step
- 14 March 2006
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 71 (8) , 3287-3290
Abstract
The synthesis of (−)-stemoamide was achieved in 11 steps from 5-acetoxy-N-crotyl pyrrolidinone. A chiral N-acyl thiazolidinethione was employed in a stereoselective addition to a cyclic N-acyl iminium ion to install the required stereochemistry of carbon C9a. This iminium ion addition product was employed in a stereoselective MgBr2-catalyzed anti-aldol reaction to install the required stereochemistry of carbons C8 and C9. The X-ray crystal analysis of (−)-stemoamide confirmed the structure and the stereochemical outcome of these selective reactions.Keywords
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