Total synthesis of tryprostatins A and B

Takayuki Yamakawa, Eiji Ideue, Yuzo Iwaki, Ayumu Sato, Hidetoshi Tokuyama, Jun Shimokawa, Tohru Fukuyama

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fürstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.

Original languageEnglish
Pages (from-to)6547-6560
Number of pages14
JournalTetrahedron
Volume67
Issue number35
DOIs
Publication statusPublished - 2011 Sep 2

Keywords

  • Alkaloids
  • Natural product
  • Radical cyclization
  • Total Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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