Bioinspired Total Synthesis of the Dimeric Indole Alkaloid (+)-Haplophytine by Direct Coupling and Late-Stage Oxidative Rearrangement

Hitoshi Satoh, Ken Ichi Ojima, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

A bioinspired convergent total synthesis of (+)-haplophytine, a dimeric indole alkaloid with diazabicyclo[3.3.1]nonane and hexacyclic aspidosperma segments, is described. This synthesis involves the direct coupling of the two segments in a AgNTf2-mediated Friedel–Crafts reaction and construction of the diazabicyclo[3.3.1]nonane skeleton through late-stage chemoselective aerobic oxidation of the 1,2-diaminoethene moiety and a sequential semipinacol-type rearrangement.

Original languageEnglish
Pages (from-to)15157-15161
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number48
DOIs
Publication statusPublished - 2016 Nov 21

Keywords

  • Friedel–Crafts reaction
  • alkaloids
  • oxidation
  • rearrangement
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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