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7442997 
Journal Article 
SYNTHESIS OF (-)-ESERMETHOLE AND (+)-ESERMETHOLE VIA CHEMICAL RESOLUTION OF 1,3-DIMETHYL-3-(2-AMINOETHYL)-5-METHOXYOXINDOLE 
Pallavicini, M; Valoti, E; Villa, L; Lianza, F 
1994 
1 
Tetrahedron: Asymmetry
ISSN: 0957-4166 
5 
1 
111-116 
English 
WOS:A1994MT54600022 
A new synthesis of (-)- and (+)-esermethole (2 and 7 respectively), penultimate intermediates to (-)- and (+)-physostigmine, is described. Phase-transfer catalyzed dimethylation of 3-cyanomethyl-5-methoxyoxindole (3) and successive hydrogenation of the cyano group gave 1,3-dimethyl-3-(2-aminoethyl)-5-methoxyoxindole (5), which was efficiently resolved with optically active tartaric acids. Subsequent conversion to a carbamate and reductive cyclization performed by a standard method afforded both the enantiomers of esermethole. The enantiomeric excesses, determined by chiral HPLC analysis, were greater than 99.5%. In particular, analytical HPLC resolution of 5, previously reported as unfeasible, was achieved. © 1994. 
esermethole; indole derivative; physostigmine; unclassified drug; article; drug synthesis; enantiomer; high performance liquid chromatography; priority journal 
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