Catalytic Asymmetric Assembly of Stereodefined Propionate Units: An Enantioselective Total Synthesis of (−)-Pironetin
- 19 May 2006
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (23), 7438-7439
- https://doi.org/10.1021/ja061938g
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.Keywords
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