11-Step Enantioselective Synthesis of (-)-Lomaiviticin Aglycon

被引：65

作者：

Herzon, Seth B. ^{[1
]}

Lu, Liang ^{[1
]}

Woo, Christina M. ^{[1
]}

Gholap, Shivajirao L. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 19期

基金：

美国国家科学基金会;

关键词：

KINAMYCIN-F; LOMAIVITICIN-A; ENOL ETHERS; ANTITUMOR ANTIBIOTICS; NATURAL-PRODUCTS; MECHANISM; 1,4-DIKETONES; INSIGHTS; MODEL; CORE;

D O I：

10.1021/ja200034b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Lomaiviticins A and B are complex antitumor antibiotics that were isolated from a strain of Micromonospora. A confluence of several unusual structural features renders the lomaiviticins exceedingly challenging targets for chemical synthesis. We report an 11-step, enantioselective synthetic route to lomaiviticin aglycon. Our route proceeds by late-stage, stereoselective dimerization of two equivalent monomeric intermediates, a transformation that may share parallels with the natural products' biosyntheses. The route we describe is scalable and convergent, and it lays the foundation for determination of the mode of action of these natural products.

引用

收藏

页码：7260 / 7263

页数：4

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