Total Synthesis of (±)-Streptonigrin: De Novo Construction of a Pentasubstituted Pyridine using Ring-Closing Metathesis

被引：50

作者：

Donohoe, Timothy J. ^{[1
]}

Jones, Christopher R. ^{[1
]}

Barbosa, Luiz C. A. ^{[2
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

[2] Univ Fed Vicosa, Dept Chem, BR-36570000 Vicosa, MG, Brazil

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 41期

关键词：

CROSS-COUPLING STRATEGIES; STREPTONIGRIN; LAVENDAMYCIN; DEGRADATION; DERIVATIVES; CONNECTION; METALATION; ANALOGS; AGENTS; DNA;

D O I：

10.1021/ja207835w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the potent antitumor agent (+/-)-streptonigrin has been achieved in 14 linear steps and 11% overall yield from ethyl glyoxalate. The synthesis features a challenging ring-closing metathesis reaction, followed by elimination and aromatization, to furnish a key pentasubstituted pyridine fragment.

引用

页码：16418 / 16421

页数：4

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