Synthesis of (2R,4S,5S)-Epiallomuscarine, (2S,3R,5S)-Isoepiallomuscarine, and (2S,3S,4S,5S)-3-Hydroxyepiallomuscarine from α-D-Glucose

Article abstract of DOI:10.1021/jo01314a031

(2R,4S,5S)-Epiallomuscarine iodide (4) and two new muscarine analogues (5 and 6) have been synthesized from α-D-glucose.Furanose 10, obtained in 64percent overall yield from α-D-glucose, was reduced by lithium aluminum hydride to afford a 3:2 mixture of alcohols (11a and 11b).Acetylation of 11a gave acetate 13.Hydrolysis of 13 was followed by oxidation to carboxylic acid 14, which upon treatment with oxalyl chloride and subsequent treatment with dimethylamine afforded dimethylamide 15.Reduction of 15 with lithium aluminim hydride and quarternization of the product amine with methyl iodide afforded 4.The same methodology was employed to synthesize (2S,3,R,5S)-isoepiallomuscarine (5) and (2S,3S,4S,5S)-3-hydroxyepiallomuscarine (6).