New carbamate analogs of (-)-physostigmine were prepared from (-)-eseroline and various isocyanates, including optically active 1- phenylethyl isocyanates. N-Benzylation of (-)-N1-noreseroline O- methylether prepared by total synthesis afforded N1- benzylnorphysostigmine, after O-demethylation and reaction with N-methylisocyanate, and N1-norphysostigmine after catalytic debenzylation over Pd-catalyst in methanol. A larger quantity of (+)-physostigmine was prepared by total synthesis, using for purification of intermediates and end product fumarate and salicylate salts and avoiding column chromatography.

Project Start
Project End
Budget Start
Budget End
Support Year
2
Fiscal Year
1987
Total Cost
Indirect Cost
Name
U.S. National Inst Diabetes/Digst/Kidney
Department
Type
DUNS #
City
State
Country
United States
Zip Code