摘要/Abstract

研究了1-苯甲酰基-3，4-二氢异喹啉生物碱的一条新的合成路线.以3，4-二甲氧基苯甲醛为起始原料，通过6步反应，以50%的总收率首次全合成得到生物碱Nelumstemine；另外，以香兰醛为起始原料，通过9步反应，以35%的总收率首次全合成得到生物碱Longifolonine.上述全合成的关键步骤为，可见光照射下1-苄基-3，4-二氢异喹啉在室温下被空气氧化为1-苯甲酰基-3，4-二氢异喹啉的反应，并对此温和的光化学反应进行了详细研究.
关键词: 苯甲酰基二氢异喹啉生物碱, 光氧化, Nelumstemine, Longifolonine
A novel synthetic route for the total syntheses of 1-benzoyl-3,4-dihydroisoquinoline alkaloids was developed. Nelumstemine was synthesized for the first time via 6 steps in 50% overall yield starting from 3,4-dimethoxybenzaldehyde, and longifolonine was also synthesized for the first time via 9 steps in 35% overall yield starting from vanillin. The key step of these total syntheses is photo-oxidation of 1-benzyl-3,4-dihydroisoquinolines to 1-benzoyl-3,4-dihydroisoquinolines by air under visible-light irradiation at room temperature. The unique mild photo-oxidation of 1-benzyl-3,4-dihydro-isoquinolines has been studied in detail.
Key words: benzoyl dihydroisoquinoline alkaloids, photo-oxygenation, nelumstemine, longifolonine


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