Catalytic Asymmetric Assembly of Stereodefined Propionate Units: An Enantioselective Total Synthesis of (−)-Pironetin
Journal of the American Chemical Society2006Vol. 128(23), pp. 7438–7439
Citations Over TimeTop 10% of 2006 papers
Abstract
Double diastereoselection in alkaloid-catalyzed acyl halide-aldehyde cyclocondensation (AAC) reactions provides a strategy for realizing syn- or anti-selective propionate aldol additions from a common reaction manifold. Matched AAC homologation of enantioenriched aldehydes afford cis-disubstituted beta-lactones as surrogates for syn aldols; the mismatched AAC reactions provide anti-selective aldols in the form of trans-disubstituted 2-oxetanones. The utility of this reaction technology in synthesis activities is exemplified in a catalytic asymmetric total synthesis of (-)-pironetin.
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