Total Synthesis of Aquayamycin

被引：15

作者：

Kusumi, Shunichi ^{[1
]}

Nakayama, Harunobu ^{[1
]}

Kobayashi, Takumi ^{[1
]}

Kuriki, Hajime ^{[1
]}

Matsumoto, Yuka ^{[1
]}

Takahashi, Daisuke ^{[1
]}

Toshima, Kazunobu ^{[1
]}

机构：

[1] Keio Univ, Fac Sci & Technol, Dept Appl Chem, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 52期

关键词：

angucycline antibiotics; antitumor antibiotics; aquayamycin; natural products; total synthesis; ANGUCYCLINE ANTIBIOTICS; RING; DERIVATIVES; CLEAVAGE; DEAROMATIZATION; SAQUAYAMYCINS; STREPTOMYCES; INHIBITORS; ALDEHYDES; EFFICIENT;

D O I：

10.1002/chem.201604697

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 diastereo-selective 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.

引用

页码：18733 / 18736

页数：4

共 39 条

[1] Retymicin, galtamycin B, saquayamycin Z and ribofuranosyllumichrome, novel secondary metabolites from Micromonospora sp Tu 6368 -: I.: Taxonomy, fermentation, isolation and biological activities [J].