Synthesis and Diels-Alder reactions of 1, 3-dimethyl-4-(phenylsulfonyl)-4H-furo [3, 4-b] indole. A new annulation strategy for the construction of ellipticine and …

…, MG Saulnier, MP Sibi, JA Obaza-Nutaitis

文献索引：Gribble, Gordon W.; Saulnier, Mark G.; Sibi, Mukund P.; Obaza-Nutaitis, Judy A. Journal of Organic Chemistry, 1984 , vol. 49, # 23 p. 4518 - 4523

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被引用次数: 116

摘要

The novel fused heterocycle 1, 3-dimethyl-4-(phenylsulfonyl)-4H-furo [3, 4-b] indole(4) is synthesized from 3-ethylindole (6) in six steps (46% yield) or from indole-3-carboxaldehyde (12) in four steps (21% yield). Furoindole 4 undergoes Diels-Alder reactions with dimethyl acetylenedicarboxylate, N-phenylmaleimide, benzyne, and 3, 4-pyridyne (5) to give the expected adducts 17, 18a, b, 19, and 23a, b, respectively. Deoxygenation and ...