Zhai Hongbin, Luo Shengjun, Ye Chengfeng, Ma Yongxiang
Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China.
J Org Chem. 2003 Oct 17;68(21):8268-71. doi: 10.1021/jo0348726.
8O-methylaphanorphine was synthesized from 4-methoxyphenylacetaldehyde in 36% overall yield and in nine steps, featuring the formation of ring B via a Friedel-Crafts alkylative cyclization with the concomitant stereospecific introduction of the benzylic quaternary carbon center. The current work constitutes an efficient enantioselective formal synthesis of 3-benzazepine marine alkaloid (-)-aphanorphine.
8-O-甲基阿法诺啡以4-甲氧基苯乙醛为原料，经九步反应合成，总收率为36%，其特征在于通过傅克烷基化环化反应形成B环，并同时立体定向引入苄基季碳中心。目前的工作构成了3-苯并氮杂卓类海洋生物碱（-）-阿法诺啡的高效对映选择性形式合成。
