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<p>This research focuses on developing efficient synthetic methodologies for the construction of complex heterocyclic ring systems. Novel cyclization reactions are employed as key strategies. A new synthetic route to 1,5-methanoazocino[4,3-b]indole is described, utilizing a Fischer indole cyclization of 2-(3-oxocyclohexyl)acetonitrile, which forms the tetracyclic framework characteristic of an important subgroup of Strychnos alkaloids. This method employs 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for a cyclization reaction involving tetrahydrocarbazole with a monoalkyl nitrile side chain at the C-2 position. The resulting ABCD-ring system, found in Strychnos alkaloids, is thus generated. The synthesized compounds are characterized using spectroscopic techniques, and the 1,5-methanoazocino[4,3-b]indole synthesis is completed in five steps (60% overall yields) and thereby affords compounds <b>2</b> (85%), <b>3</b> (91%), <b>5</b> (94%), <b>6</b> (98%), and <b>7</b> (84%), respectively.</p>

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A New Method for the Construction of the 1,5-Methanoazocino[4,3-b]indole Rings of Strychnos Alkaloids

  • 期刊论文

  • 发表日期：

    2025年7月10日

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  • Nesimi Uludag,
  • Omer Karabudak

摘要

This research focuses on developing efficient synthetic methodologies for the construction of complex heterocyclic ring systems. Novel cyclization reactions are employed as key strategies. A new synthetic route to 1,5-methanoazocino[4,3-b]indole is described, utilizing a Fischer indole cyclization of 2-(3-oxocyclohexyl)acetonitrile, which forms the tetracyclic framework characteristic of an important subgroup of Strychnos alkaloids. This method employs 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for a cyclization reaction involving tetrahydrocarbazole with a monoalkyl nitrile side chain at the C-2 position. The resulting ABCD-ring system, found in Strychnos alkaloids, is thus generated. The synthesized compounds are characterized using spectroscopic techniques, and the 1,5-methanoazocino[4,3-b]indole synthesis is completed in five steps (60% overall yields) and thereby affords compounds 2 (85%), 3 (91%), 5 (94%), 6 (98%), and 7 (84%), respectively.