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Paper | Special issue | Vol 97, No. 2, 2018, pp.865-876
Published online, 28th May, 2018
DOI: 10.3987/COM-18-S(T)64
Asymmetric Synthesis of O-Methylneferine

Katsumi Nishimura,* Shinji Horii, and Takao Tanahashi

*Organic Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita-machi, Higashinada-ku, Kobe 658-8558, Japan


Diastereoselective Pictet–Spengler reaction of 2-arylethylamine bearing an N-(R)-1-(1-naphthyl)ethylcarbamoyl group with arylacetaldehyde gave 1-benzyltetrahydroisoquinoline in good yield with moderate diastereoselectivity. The reaction was applied to asymmetric synthesis of O-methyl derivative of neferine, an alkaloid of the lotus embryo, Nelumbo nucifera Gaertner.