CHEMISTRY OF NATURAL COMPOUNDS, AND SYNTHETIC ORGANIC CHEMISTRY

天然化合物化学和有机合成化学

• 批准号: 3917715
• 负责人: U WEISS
• 金额: --
• 依托单位: NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES
• 依托单位国家: 美国
• 资助国家: 美国
• 起止时间: 至
• 项目状态: 未结题
• 来源: https://reporter.nih.gov/project-details/3917715
• 关键词: X ray crystallography; alkaloids; carbonyl compound; chemical structure; chemical synthesis; circular dichroism; cyclopentane; diene; drug screening /evaluation; glutarates; heterocyclic polycyclic compound; infrared spectrometry; nuclear magnetic resonance spectroscopy; pigments; plant extracts; quinones; radiosensitizer; sesquiterpenes; stereochemistry; ultraviolet spectrometry; xanthines

In continued cooperation with Prof. J.M. Cook and his coworkers at the University of Wisconsin-Milwaukee, the synthesis of di-and ploycyclic ring systems composed of fused cyclopentane rings ("polyquinanes") has been developed further. The approach chosen is based on the ready stereosoecific formation of derivatives of cis-bicylo (3.3.0) octane-3.7-dione (1) from 1.2-dicarbonyl compounds and esters of 3-oxoglutaric acid (the "Weiss reaction"). Several more tetracyclic polyquinane ring systems have been synthesized by suitable further transformations of (1) or its closely related analogs. Thus, the first 1, 10-disubstituted derivatives of the long-known, triply unsaturated triquinane triquinacence (R.B. Woodward et al., 1964) have been made, including a novel compound,2, where an additional six-membered ring is fused at these positions of triquinacene. Saturated representatives of several other systems have been prepared as intermediates in the planned synthesis of related compounds with the maximum possible number of double bonds; these latter molecules should be valuable for intended studies of the possible aromatic nature of such compounds.

继续与J.M.库克教授和他的同事在 威斯康星大学密尔沃基分校的双和 稠环戊烷环组成的多环环体系 (“多喹烷”)有了进一步的发展。所选择的方法 是基于现成的立体定向形成的衍生物 1.2-二羰基顺式-二烷基(3.3.0)辛烷-3.7-二酮(1) 3-氧代戊二酸的化合物和酯(“Weiss反应”)。 几个更多的四环多喹烷环体系已经被 由(1)或其适当的进一步变换合成的 密切相关的类比。因此，第一个1，10-二取代 已知的三重不饱和三喹烷的衍生物 三个五元环(R.B.Woodward等人，1964)， 包括一种新的化合物2，其中另一个六元环 在三苯并二苯的这些位置上熔合。饱和 其他几个系统的代表已经准备好 有计划地合成相关化合物的中间体 双键的最大可能数目；后一种分子 应该对可能的芳香族化合物的预期研究有价值 这类化合物的性质。