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Asymmetric Total Synthesis of (S)-(+)-Cocaine and the First Synthesis of Cocaine C-1 Analogs from N-Sulfinyl β-Amino Ester Ketals

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journal contribution
posted on 2010-09-17, 00:00 authored by Franklin A. Davis, Naresh Theddu, Ram Edupuganti
Sulfinimine-derived α,β-unsaturated pyrrolidine nitrones, on heating with Al(O-t-Bu)3, undergo a highly stereoselective intramolecular [3 + 2] cycloaddition to give tricyclic isoxazolidines, which are transformed in three-steps to give C-1 substituted cocaine analogs.