Collect. Czech. Chem. Commun. 1998, 63, 1522-1527

Stereospecific Synthesis of (+)-Muscarine from D-Glucose, Suitable for Preparation of 5-Substituted Analogues

Velimir Popsavin, Ostoja Beric, Ljubica Radic, Mirjana Popsavin, Vera Cirin-Novta and Dušan Miljković

Institute of Chemistry, Faculty of Sciences, University of Novi Sad, Trg D. Obradovica 3, 210 00 Novi Sad, Yugoslavia


A stereospecific synthesis of (+)-muscarine iodide (1) has been achieved starting from D-glucose as a chiral precursor. The key steps of the synthesis involved a stereospecific cyclization of 3,5-di-O-mesyl derivative 3 into the 2,5-anhydride 4, the stereospecific catalytic hydrogenation of unsaturated derivative 6, and the C-4 epimerization of alcohol 12 by Mitsunobu reaction.

Keywords: 2,5-Anhydro sugars; (+)-Muscarine, Stereospecific synthesis; Alkaloids; Carbohydrates.