Total Synthesis of Aquayamycin

Shunichi Kusumi, Harunobu Nakayama, Takumi Kobayashi, Hajime Kuriki, Yuka Matsumoto, Daisuke Takahashi, Kazunobu Toshima

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereoselective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.

Original languageEnglish
Pages (from-to)18733-18736
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number52
DOIs
Publication statusPublished - 2016 Dec 23

Keywords

  • angucycline antibiotics
  • antitumor antibiotics
  • aquayamycin
  • natural products
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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