Novel zinc-promoted alkylation of iminium salts. New synthesis of benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids and related compounds

T Shono, H Hamaguchi, M Sasaki…

文献索引：Shono, Tatsuya; Hamaguchi, Hiroshi; Sasaki, Manji; Fujita, Shumei; Nagami, Kimihiko Journal of Organic Chemistry, 1983 , vol. 48, # 10 p. 1621 - 1628

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被引用次数: 47

摘要

Zinc-promoted reductive coupling reaction of iminium salts with alkyl halides was found to be a successful key reaction for synthesis of a variety of alkaloids such as benzylisoquinoline, phthalidylisoquinoline, and protoberberine alkaloids. More specifically, laudanosine, cordrastine, hydrastine, narcotine, tetrahydropalmatine, and canadine were obtained. A new route for the synthesis of the emetine and yohimbine skeletons was ...