合成路线1

The isomerization of arecoline (I) with LDA gives 1-methyl-1,2,3,6-tetrahydropyridine-3-carboxylic acid methyl ester (II), which is reduced with LiAlH4 in THF yielding the carbinol (III). The protection of (III) with trichloroethyl chloroformate (Troc-Cl) and DIEA in toluene affords the demethylated compound (IV), which is treated with K2CO3 in methanol providing 3-(hydroxymethyl)-1,2,3,6-tetrahydropyridine-1-carboxylic acid 2,2,2-trichloroethyl ester (V). The silylation of (V) with TBDPSCl and imidazole in DMF gives the silyl ether (VI), which is epoxidized with MCPBA in dichloromethane yielding the epoxide (VII). Epoxide (VII) opening by means of HClO4 in refluxing water affords a diastereomeric mixture of racemates (VIII) and (IX) that could not be separated. The cleavage of the carbamate group of (VIII) and (IX) by means of HCl in water gives a new mixture that could be separated by flash chromatography to furnish the target compound as a racemate. Alternatively, intermediate (IV) is epoxidized with MCPBA in dichloromethane yielding the epoxide (X), which is treated as before.