2. Academic Validation
  3. Total Synthesis of Aquayamycin

Total Synthesis of Aquayamycin

  • Chemistry. 2016 Dec 23;22(52):18733-18736. doi: 10.1002/chem.201604697.
Shunichi Kusumi 1,  Harunobu Nakayama 1,  Takumi Kobayashi 1,  Hajime Kuriki 1,  Yuka Matsumoto 1,  Daisuke Takahashi 1,  Kazunobu Toshima 1
Affiliations

Affiliation

  • 1 Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, 223-8522, Japan.
PMID: 27859867 DOI: 10.1002/chem.201604697
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.

Keywords

angucycline antibiotics; antitumor antibiotics; aquayamycin; natural products; total synthesis.

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