Synthesis of (−)-Stemoamide Using a Stereoselective anti-Aldol Step
The Journal of Organic Chemistry2006Vol. 71(8), pp. 3287–3290
Citations Over TimeTop 11% of 2006 papers
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.
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