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

UK Bandarage, ME Kuehne, SD Glick

Index: Bandarage, Upul K.; Kuehne, Martin E.; Glick, Stanley D. Tetrahedron, 1999 , vol. 55, # 31 p. 9405 - 9424

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Citation Number: 28

Abstract

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-ζ-(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 ...