Total Synthesis of Aquayamycin

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

Research output: Contribution to journalArticle

6 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

Fingerprint

Allylation
Antibiotics
Ketones
Indium
Naphthoquinones
Anti-Bacterial Agents
aquayamycin

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Kusumi, S., Nakayama, H., Kobayashi, T., Kuriki, H., Matsumoto, Y., Takahashi, D., & Toshima, K. (2016). Total Synthesis of Aquayamycin. Chemistry - A European Journal, 22(52), 18733-18736. https://doi.org/10.1002/chem.201604697

Total Synthesis of Aquayamycin. / Kusumi, Shunichi; Nakayama, Harunobu; Kobayashi, Takumi; Kuriki, Hajime; Matsumoto, Yuka; Takahashi, Daisuke; Toshima, Kazunobu.

In: Chemistry - A European Journal, Vol. 22, No. 52, 23.12.2016, p. 18733-18736.

Research output: Contribution to journalArticle

Kusumi, S, Nakayama, H, Kobayashi, T, Kuriki, H, Matsumoto, Y, Takahashi, D & Toshima, K 2016, 'Total Synthesis of Aquayamycin', Chemistry - A European Journal, vol. 22, no. 52, pp. 18733-18736. https://doi.org/10.1002/chem.201604697
Kusumi S, Nakayama H, Kobayashi T, Kuriki H, Matsumoto Y, Takahashi D et al. Total Synthesis of Aquayamycin. Chemistry - A European Journal. 2016 Dec 23;22(52):18733-18736. https://doi.org/10.1002/chem.201604697
Kusumi, Shunichi ; Nakayama, Harunobu ; Kobayashi, Takumi ; Kuriki, Hajime ; Matsumoto, Yuka ; Takahashi, Daisuke ; Toshima, Kazunobu. / Total Synthesis of Aquayamycin. In: Chemistry - A European Journal. 2016 ; Vol. 22, No. 52. pp. 18733-18736.
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