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Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine


, : Total syntheses of racemic albifloranine and its anti-addictive congeners, including 18-methoxycoronaridine. Tetrahedron 55(31): 9405-9424, July 30

Condensation of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino(4,5-b)indole-5-carboxylate (12) with 4-(1,3-dioxolan-2-yl)-6-benzyloxyhexanal (11a) provided the tetracyclic intermediates methyl (3aSR,4RS,11bRS)-3-benzyl-2,3,3a,4,5,7-hexahydro-4-(2-zeta-(1,3-dioxalan-2-yl)-4-benzyloxy)-1-butyl)-1H-pyrrolo(2,3-d)carbazole-6-carboxylates (14a,15a), which were further elaborated to afford racemic albifloranine (3). The first total synthesis of albifloranine was completed in 13 steps, with an overall 7% yield. Ester and ether derivatives of albifloranine were synthesized for evaluation as anti-addictive agents. Among these, 18-methoxycoronaridine (20b) stands out as a nontoxic agent that significantly reduces demand for morphine, cocaine, nicotine and alcohol in rats.

US$19.90

DOI: 10.1016/s0040-4020(99)00513-x


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