- Total Synthesis of Tetrahydroisoquinoline-Based Bioactive Natural Products Laudanosine, Romneine, Glaucine, Dicentrine, and Their Unnatural Analogues Isolaudanosine and Isoromneine
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Starting from suitably substituted homophthalic acids, total synthesis of titled alkaloids have been demonstrated in very good yields. The obtained natural products laudanosine and romneine were utilized to accomplish synthesis of two isoquinoline-based alkaloids glaucine and dicentrine. Base-induced selective generation of two different types of benzylic carbanions, their coupling reactions with 3,4-dimethoxybenzyl mesylate, and the regioselective iodination followed by intramolecular aryl-aryl coupling reactions to form the fused biaryl systems were the strategic steps.
- Jangir, Ravi,Argade, Narshinha P.
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- Identification of N-benzyltetrahydroisoquinolines as novel anti-neuroinflammatory agents
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A series of simplified berberine analogs was designed, synthesized, and evaluated for anti-inflammatory activity. SAR studies identified N-benzyltetrahydroisoquinoline 7d as a potent berberine analog. 7d suppressed LPS-induced inflammatory cytokine levels
- Gabet, Brian,Kuo, Ping-Chang,Fuentes, Steven,Patel, Yamini,Adow, Ahmed,Alsakka, Mary,Avila, Paula,Beam, Teri,Yen, Jui-Hung,Brown, Dennis A.
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p. 5711 - 5717
(2018/10/26)
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- Synthesis of Benzyltetrahydroisoquinoline Alkaloids with the Use of 1,3-Dithianes of Aromatic Aldehydes
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A practical synthesis of 1-benzyl-2-methyl-1,2,3,4-tetrahydroisoquinolines (4) is described. Condensation of 6,7-disubstituted N-methyl-3,4-dihydroisoquinolinium iodide 1 with 1,3-dithianes 2 gave addition products 3 from which alkaloids 4 were obtained by desulfuration. Key words: 1-benzyltetrahydroisoquinolines, dithianes, tetrahydroisoquinolinium alkaloids
- Brozda, D.
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p. 2665 - 2670
(2007/10/02)
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