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■ Total Synthesis of Sinomendine and Its Analogs

De-Min Zhou, Bao-Zhen Yue, Ji-Qiao Cui, Meng-Shen Cai, and Li-He Zhang*

*School of Pharamceutical Sciences, Beijing Medical University, Beijing, 100083, China

Abstract

Sinomendine (1), a good receptor antagonist of angiotensin II and rare oxoaporphine alkaloid isolated from traditional Chinese drug Sinomenium acutum (Thunb.) Rehd. et Wils, was synthesized from a bromobenzylidenetetrahydroisoquinolineenamide precursor (6). Photocyclization of this enamide led to a protected aporphine (7), which could be converted into oxoaporphine (9) and (±)-sinomendine (1) by Fremy’s salt oxidation followed an available Grignard reaction.