Remodeling of Fumagillol: Discovery of an Oxygen-Directed Oxidative Mannich Reaction

被引：20

作者：

Grenning, Alexander J. ^{[1
]}

Snyder, John K. ^{[1
]}

Porco, John A., Jr. ^{[1
]}

机构：

[1] Boston Univ, Ctr Chem Methodol & Lib Dev, Boston, MA 02215 USA

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 03期

基金：

美国国家卫生研究院;

关键词：

DIVERSITY-ORIENTED SYNTHESIS; DEHYDROGENATIVE COUPLING REACTIONS; NATURAL-PRODUCTS; STEREOCHEMICALLY COMPLEX; REGIOSELECTIVE OXIDATION; ORGANIC-SYNTHESIS; DDQ; FUMIQUINAZOLINE; GENERATION; SCAFFOLDS;

D O I：

10.1021/ol4035269

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which. mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of the basic fumagillol scaffold with a variety of readily available coupling partners. Mechanistic experiments leading to the discovery of an oxygen-directed oxidative Mannich reaction are also described.

引用

页码：792 / 795

页数：4

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