New strategy for the syntheses of (+/-)-latifine and (+/-)-cherylline dimethyl ethers

Abstract

A concise route for the synthesis of (+/-)-latifine and (+/-)-cherylline dimethyl ethers is reported. The key steps involved are the Michael type addition of p-methoxybenzene magnesium bromide to the (E)-1,2-dimethoxy-3-(2- nitrovinyl)benzene, reduction of the nitro intermediate obtained followed by the Pictet-Spengler cyclization and reductive N-methylation.