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| - Enantiospecific and Stereoselective Synthesis of PolyhydroxylatedPyrrolidines and Indolizidines from trans-4-Hydroxy-l-proline
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| - We have developed a short, efficient, and stereoselectivesynthesis of polyhydroxylated pyrrolidineand indolizidine glycosidase inhibitors starting from4-hydroxy-l-proline. The regio- andstereoselective hydroxylation of an N-Pf-4-oxoproline enolate andthe stereoselective reduction of theresulting keto alcohol allowed us to introduce the cis diolpresent in the target compounds. Thedifferent side chains needed to complete the syntheses of the targetcompounds were introducedby reduction of the ester group of a substituted proline or by reactionof organolithium ororganomagnesium reagents with the same group followed bystereoselective reduction of theresulting ketones. Hydrogenolysis of the alcohols thus obtainedgave the hydrochlorides of thedesired pyrrolidine glycosidase inhibitors, which were obtained in ninesteps in overall yields greaterthan 50%. The indolizidine glycosidase inhibitor8-epi-swainsonine was also prepared using thisapproach.
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