Organic letters

Total Synthesis of (±)-Herbindole B and (±)-cis-Trikentrin B

SK Jackson, SC Banfield, MA Kerr

Index: Jackson, Stephen K.; Banfield, Scott C.; Kerr, Michael A. Organic Letters, 2005 , vol. 7, # 7 p. 1215 - 1218

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Citation Number: 66

Abstract

Herbindole B and cis-trikentrin B are naturally occurring indoles having the unusual and synthetically challenging pattern of carbon substitution at the 4-7 and 5-7 positions, respectively, with no substitution at the 1-3 positions. The total syntheses of these polyalkylated indoles have been achieved in 19 and 12 steps, respectively. The synthesis of herbindole B relies on two iterations of a quinine monoimine Diels-Alder reaction, while ...