Stereoselective syntheses of the three isomers of ethylene glycol bis (tropane-3-carboxylate)

J Cheng, Z Moore, ED Stevens…

文献索引：Cheng, Jie; Moore, Zakhia; Stevens, Edwin D.; Trudell, Mark L. Journal of Organic Chemistry, 2002 , vol. 67, # 15 p. 5433 - 5436

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被引用次数: 14

摘要

Three epimers of ethylene glycol bis (tropane-3-carboxylate)(3α, 3α'-, 3α, 3β'-, 3β, 3β'-) have been synthesized by starting from 3-tropinone. 3-Tropinone was converted into the corresponding enol triflate and then subjected to palladium-catalyzed alkoxycarbonylation to provide the key intermediate methyl trop-2-ene-3-carboxylate in good yield. Stereoselective routes were developed to afford the three stereoisomers of ethylene glycol bis (tropane-3- ...