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Fukuyama indole synthesis

Introduction

Overview

Overview

The Fukuyama indole synthesis is the chemical reaction of alkenylthioanilides to give 2,3-disubstituted indoles.[1] Most commonly tributyltin hydride is utilized as the reducing agent, with azobisisobutyronitrile (AIBN) as a radical initiator.

The Fukuyama indole synthesis
The Fukuyama indole synthesis

Being one of the simplest methods for synthesizing poly-substituted indoles, this procedure has been utilized in numerous natural product syntheses, including aspidophytine[2], vinblastine[3], and strychnine[4].

References

References

  1. ↑ Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 1999, 121, 3791-3792. (doi:10.1021/ja983681v)
  2. ↑ Sumi, S.; Matsumoto, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 1891-1893. (doi:10.1021/ol034445e)
  3. ↑ Yokoshima, S.; Ueda, T.; Kobayashi, S.; Sato, A.; Kuboyama, T.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 2137-2139. (doi:10.1021/ja0177049)
  4. ↑ Kaburagi, Y.; Tokuyama, H.; Fukuyama, T. J. Am. Chem. Soc. 2004, 126, 10246-10247. (doi:10.1021/ja046407b)


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