Total Synthesis of (-)-Isoschizogamine

Akihiro Takada, Hiroaki Fujiwara, Kenji Sugimoto, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The total synthesis of (-)-isoschizogamine was accomplished, featuring the construction of the quaternary carbon center by the modified Johnson-Claisen rearrangement in basic media and the facile assembly of the key tetracyclic quinolone intermediate through a cascade cyclization. The characteristic cyclic aminal was constructed by late-stage C-H functionalization at the position adjacent to the lactam nitrogen using a combination of CrO3 and nBu4NIO4 and subsequent Bi(OTf)3-mediated cyclization.

Original languageEnglish
Pages (from-to)16400-16403
Number of pages4
JournalChemistry - A European Journal
Volume21
Issue number46
DOIs
Publication statusPublished - 2015 Nov 1

Keywords

  • C-H functionalization
  • alkaloids
  • aminal
  • cascade reaction
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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