Stereochemical Determination of the Leupyrrins and Total Synthesis of Leupyrrin A1

被引：23

作者：

Herkommer, Daniel ^{[1
]}

Thiede, Sebastian ^{[1
]}

Wosniok, Paul R. ^{[1
]}

Dreisigacker, Sandra ^{[1
]}

Tian, Maoqun ^{[1
]}

Debnar, Thomas ^{[1
]}

Irschik, Herbert ^{[2
]}

Menche, Dirk ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

[2] Helmholtz Ctr Infect Res HZI, Microbial Drugs, D-38124 Braunschweig, Germany

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 12期

关键词：

ESTERS; ISOMERS;

D O I：

10.1021/jacs.5b01894

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The stereochemical determination of the potent antifungal agents leupyrrin A(1) and B-1 and the total synthesis of leupyrrin A(1) are reported. The relative and absolute configuration was determined by a combination of high field NMR studies, molecular modeling, and chemical derivatization. The expedient total synthesis involves a one-pot sequential Zr-mediated oxidative diyne-cyclization/regioselective opening sequence for preparation of the unique dihydrofuran ring, a highly stereoselective one-pot approach to the butyrolactone, a challenging sp(2)-sp(3) Suzuki coupling and a high-yielding Shiina macrolactonization.

引用

页码：4086 / 4089

页数：4

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