The Journal of organic chemistry

An Efficient Synthesis of 4-(Phenylsulfonyl)-4 H-furo [3, 4-b] indoles

GW Gribble, J Jiang, Y Liu

文献索引：Gribble, Gordon W.; Jiang, Jun; Liu, Yanbing Journal of Organic Chemistry, 2002 , vol. 67, # 3 p. 1001 - 1003

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被引用次数: 26

摘要

The fused heterocycle 4-(phenylsulfonyl)-4 H-furo [3, 4-b] indole, which is an indole-2, 3- quinodimethane synthetic analogue, is prepared in five steps from indole in 46% yield. A similar sequence is used to synthesize C-3 derivatives (3-methyl, 3-phenyl, and 3-heptyl). Thus, indole-3-carbaldehyde (1) is protected as the N-phenylsulfonyl derivative 2 and converted to the ethylene acetal 6. Lithiation at C-2 followed by treatment with an ...