Synthetic studies on indoles and related compounds. Part 46.1 First total syntheses of 4, 8-dioxygenated β-carboline alkaloids

…, M Hagiwara, T Ohyama, Y Yokoyama…

Index: Suzuki, Hideharu; Unemoto, Minoru; Hagiwara, Mayumi; Ohyama, Takako; Yokoyama, Yuusaku; Murakami, Yasuoki Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 12 p. 1717 - 1723

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Citation Number: 18

Abstract

Total syntheses of naturally occurring 4, 8-dioxygenated β-carboline alkaloids 2a, 2d, 2g, and 2h are described. The synthetic route involves two methodologies that we developed;(i) an improved Fischer indolization for the synthesis of a 7-oxygenated indole using a tosyl group for protection of the phenolic group,(ii) construction of a 4-methoxy-β-carboline skeleton by the C-3-selective cyclization of the C-2-substituent of the indole nucleus. The ...