Organic Letters 2000-07-13

A concise synthesis of topsentin A and nortopsentins B and D.

F Y Miyake, K Yakushijin, D A Horne

Index: Org. Lett. 2(14) , 2121-3, (2000)

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Abstract

[reaction: see text] A concise synthesis of topsentin A (R(1) = R(2) = H) and nortopsentins B (R(1) = Br, R(2) = H) and D (R(1) = R(2) = H) is described from oxotryptamine 5 via reduction of acyl cyanide 4. Regiospecific bromination of 3-cyanoindole afforded 6-bromo-3-cyanoindole (10) as the major product.