新产品编号:2319721

Chemical Name: Benzoic acid [(3S,6Z,7S,8S,8aR)-6-(3-chloro-4-iodobenzylidene)perhydro-3,7-methanoindolizin-8-yl]methyl ester
项目整合开发状态: Biological Testing
项目研究机构: Georgetown University (Originator), UT Medical Branch at Galveston (Originator)
合成路线:N-Demethylation of cocaine (I) is accomplished by treatment with 1-chloroethyl chloroformate,followed by methanolysis of the intermediate chloroethyl carbamate.The resultant nor-cocaine (II) is alkylated with propargyl bromide (III) to afford (IV).Acidic ester hydrolysis of (IV) furnishes hydroxy acid (V).Chlorination of (V) with POCl3,followed by treatment with methanol gives rise to the unsaturated ester (VI).Radical cyclization of the enyne system (VI) in the presence of Bu3SnH and AIBN affords a Z/E mixture of tricyclic vinyl stannanes (VIIa-b) that are separated by column chromatography.The major Z isomer is then subjected to Stille coupling with the aryl iodide (VIII),yielding adduct (IX).Then,reduction of the ester function of (IX) to the primary alcohol (X) is performed by means of either LiAlH4 or DIBAL.

合成路线:Esterification of alcohol (X) with benzoyl chloride produces benzoate ester (XI).The aryl bromide moiety of (XI) is converted to the aryl stannane (XII) using hexabutyl ditin and palladium catalyst.Finally,iododestannylation of stannane (XII) furnishes the required aryl iodide.