Enantiospecific Construction of Quaternary Carbon Center via Intramolecular 1,3-Dipolar Cycloaddition. A New Route to Natural (−)-Mesembrine from (S)-O-Benzylglycidol
- 1 July 1990
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 19 (7) , 1239-1242
- https://doi.org/10.1246/cl.1990.1239
Abstract
Thermolysis of the aziridine ester, obtained from (S)-O-benzylglycidol, afforded the pyrrolidine lactone bearing a quaternary carbon center stereo-specifically in a good yield via intramolecular cycloaddition of the 1,3-dipole. The adduct (11) could be converted into natural (−)-mesembrine, the major alkaloid of Sceletium namaquense, and its N-demethyl derivative via a 8 step sequence of reactions.This publication has 13 references indexed in Scilit:
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