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Paper | Special issue | Vol 101, No. 2, 2020, pp.512-523
Published online, 24th September, 2019
DOI: 10.3987/COM-19-S(F)36
Stereoselective Construction of a Berberine C-8 Benzyl Group for the Synthesis of Javaberine Derivatives

Rina Kakigi, Mai Nakano, Ayana Ueno, Akari Miyawaki, Kiyoshi Tomioka, and Yasutomo Yamamoto*

*Faculty of Pharmaceutical Sciences, Department of Medicinal Chemistry, Doshisha Women’s College of Liberal Arts, Kodo, Kyotanabe, Kyoto 610-0395, Japan


Diastereoselective synthesis of 8-benzyltetrahydroprotoberberines was examined. Although Stevens rearrangement of N-benzylxylopinine resulted in poor yield and diastereoselectivity, benzylation of tetracyclic iminium successfully gave H8-H14 trans benzyltetrahydroprotoberberines with high stereoselectivity.