Synthetic studies on dimeric monoterpene indole alkaloid: (+) -haplophytine

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Abstract

Since dimeric indole alkaloids possess architectural diversities and a wide range of biological activities, development of new synthetic strategies for construction of these structures has been one of the important topics in synthetic chemistry. Among these compounds, we focused on an architecturally intriguing dimeric monoterpene indole alkaloid, (+) -haplophytine, which had remained an unanswered challenge for more than a quarter century in the area of alkaloid synthesis. Our first total synthesis and the second generation synthesis of (+) -haplophytine are described. The synthesis of this dimeric compound features Ag-mediated coupling reaction between two polycyclic fragments. In addition, the characteristic diazabicyclo [3.3.1] skeleton in left segment was constructed by means of creative skeletal rearrangement including oxidation step.

Original languageEnglish
Pages (from-to)418-421
Number of pages4
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume76
Issue number5
DOIs
Publication statusPublished - 2018 Jan 1

Keywords

  • Alkaloids
  • Coupling reaction
  • Diazonium salt
  • Dimeric compounds
  • Indole
  • Oxidation
  • Radical
  • Skeletal rearrangement
  • Thily
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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