白屈菜红碱的全合成

Total Synthesis of Chelerythrine

以2,3-二甲氧基-6-溴苄醇(1)为起始原料,经过6步反应合成关键中间体2,3-二甲氧基-6-碘苯甲酸甲酯(7),通过金属钯催化下与中间体(8)的串联反应策略一步构筑了白屈菜红碱的B/C环,并以10步60.9%的总收率完成了白屈菜红碱的全合成,同时对关键的金属钯催化串联反应机理进行了初步探讨,为高效合成苯并[c]菲啶类生物碱提供了一条简便路线.

Chelerythrine is an isoquinoline alkaloid isolated from Herba Chelidonii that possess complex structure and remarkable activities. In this work, its total synthetic approach was investigated. Key meditate methyl 6-iodo-2,3-dimethoxybenzoate（7） was obtained in six steps with（6-bromo-2,3-dimethoxyphenyl）methanol（1） as starting material. The core structure was efficiently constructed by palladium-catalyzed tandem reaction in one step. At the same time, a proposed mechanism of palladium-catalyzed tandem reaction was suggested and the chelerythrine was synthesized in 10 steps with a total yield of 60.9%. All compounds were confirmed by IR, 1H NMR, 13C NMR and high resolution mass spectrometer（HRMS）.