Total Synthesis of Aquayamycin

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

doi:10.1002/chem.201604697

Total Synthesis of Aquayamycin

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-review

12 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 language	English
Pages (from-to)	18733-18736
Number of pages	4
Journal	Chemistry - A European Journal
Volume	22
Issue number	52
DOIs	https://doi.org/10.1002/chem.201604697
Publication status	Published - 2016 Dec 23

Keywords

angucycline antibiotics
antitumor antibiotics
aquayamycin
natural products
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201604697

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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.",

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AU - Kusumi, Shunichi

AU - Nakayama, Harunobu

AU - Kobayashi, Takumi

AU - Kuriki, Hajime

AU - Matsumoto, Yuka

AU - Takahashi, Daisuke

AU - Toshima, Kazunobu

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KW - natural products

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Total Synthesis of Aquayamycin

Abstract

Keywords

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