APPLICATIONS OF IRON COMPLEXES TO ORGANIC SYNTHESIS

铁配合物在有机合成中的应用

• 批准号: 6385944
• 负责人: William A Donaldson
• 金额: $ 14.75万
• 依托单位: MARQUETTE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1989
• 资助国家: 美国
• 起止时间: 1989-07-01 至 2003-03-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6385944
• 关键词: alkylation; antibacterial agents; antibiotics; antifungal agents; antiviral agents; biological products; chemical synthesis; cyclopropanes; diene; drug design /synthesis /production; iron compounds; metal complex; polyenes; stereochemistry

The long range goal of our research is to develop new synthetic methodology for the construction of C-C bonds in a stereospecific fashion. This new methodology will be useful for the preparation of polyene macrolides and for the preparation of cyclopropane containing natural products. In particular, we wish to utilize the ability of an ironcarbonyl adjunct: a) to control the stereochemistry of conjugated dienes and to protect the diene against reduction oxidation, and cycloaddition reactions; b) to control the relative stereochemistry at asymmetric centers adjacent and remote to a conjugated diene; c) to control the relative stereochemistry of trisubstituted cyclopropanes; d) to control the relative stereochemistry at asymmetric centers adjacent to a trans-disubstituted cyclopropane. As vehicles for demonstration of these methodologies, we have chosen macrolactin A, madumycin II, ambruticin, 2-(2'- carboxycyclopropyl) glycines, and FR-900848 as targets. Macrolactin A was isolated from an unidentified deep sea bacterium. This compound exhibits antiviral activity against Herpes Simplex I and II and against HIV in initial tests. Since the culturing of this bacterium has been "unreliable", further biological research must rely on total synthesis. Madumycin II is a member of the streptogramin A family of antibiotics which are active against Gram-positive organisms. Ambruticin is a structurally complex antifungal agent. This compound was found to be orally active against systemic infections of histoplasmosis and coccidiomycosis. Several 2-(2'-carboxycyclopropyl)glycines have been found to be potent ligands for metabotropic glutamate receptors. FR-900848 is a polycyclopropane molecule isolated from the fermentation of Streptoverticillium fevens which inhibits filamenteous fungi such as Aspergillus niger, but has relatively low toxicity in mammals (LD50 greater than 1g/1kg).

我们研究的长远目标是开发新的合成材料

项目成果

A simple and efficient synthesis of optically pure tricarbonyl(methyl 6-oxo-2,4-hexadienoate)iron.

光学纯三羰基（6-氧代-2,4-己二烯酸甲酯）铁的简单高效合成。

• DOI: 10.1021/jo001182i
• 发表时间: 2001
• 期刊: The Journal of organic chemistry
• 作者: Godula,K;Bärmann,H;Donaldson,WA
• 通讯作者: Donaldson,WA

Reactivity of (bicyclo[5.1.0]octadienyl)iron(1+) cations: application to the synthesis of cis-2-(2'-carboxycyclopropyl)glycines.

(双环[5.1.0]辛二烯基)铁(1)阳离子的反应性：应用于顺式-2-(2-羧基环丙基)甘氨酸的合成。

• DOI: 10.1021/jo030259a
• 发表时间: 2004
• 期刊: The Journal of organic chemistry
• 作者: Wallock,NathanielJ;Donaldson,WilliamA
• 通讯作者: Donaldson,WilliamA

Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis.

无环（二烯）铁配合物和（二烯基）铁阳离子在有机合成中的最新应用。

• DOI: 10.1002/ejoc.200900141
• 发表时间: 2009
• 期刊: European journal of organic chemistry
• 影响因子: 2.8
• 作者: Donaldson,WilliamA;Chaudhury,Subhabrata
• 通讯作者: Chaudhury,Subhabrata

Iron-mediated preparation of vinylcyclopropanecarboxylates: scope, mechanism, and applications.

• DOI: 10.1021/jo020421u
• 发表时间: 2003-01
• 期刊: The Journal of organic chemistry
• 作者: Y. Yun;K. Godula;Yeyu Cao;W. Donaldson

Synthesis of lignarenone B.

木脂烯酮 B 的合成

• DOI: 10.1021/np50089a017
• 发表时间: 1992
• 期刊: Journal of natural products
• 影响因子: 5.1
• 作者: Bell,PT;Donaldson,WA
• 通讯作者: Donaldson,WA