2-Cyano-. DELTA. 3-piperideines. 13. Synthesis and reactivity of N-protected dehydrosecodine equivalents

RJ Sundberg, DS Grierson…

文献索引：Sundberg, Richard J.; Grierson, David S.; Husson, Henri-Philippe Journal of Organic Chemistry, 1984 , vol. 49, # 13 p. 2400 - 2404

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被引用次数: 16

摘要

A direct synthesis of 1-(phenylsulfony1) secodine (6) is accomplished by lithiation of l- (phenylsulfonyl)-3-[2-(5-ethyl-1, 2, 3, 6-tetrahydropyridyl) ethyl] indole (4), reaction with methyl pyruvate, and dehydration. The 2-cyano-A3-piperideine derivatives of both the carbinol precursor 9 and of 1-(phenylsulfony1) dehydrosecodine 12 have been characterized. Various reaction conditions under which 1-(pheny1sulfonyl) ...