A New, General Approach to the Synthesis of Racemic and Optically Active Morphinans

合成外消旋和旋光吗啡喃的新通用方法

• 批准号: 9315989
• 负责人: David Grove
• 金额: $ 10.47万
• 依托单位: Eckerd College
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1994
• 资助国家: 美国
• 起止时间: 1994-01-01 至 1997-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9315989&HistoricalAwards=false
• 关键词: New; General; Approach; Synthesis; Racemic

9315989 Grove The focus of the research is the use of intramolecular trapping of cobalt-stabilized propargyl cations to construct key cis-ethynyloctahydrophenanthrene intermediates. The D-ring will then be appended using an iminyl radical cyclization. The resultant advanced intermediate has the potential of providing a wide variety of N-substituted morphinans. The route is amenable to the preparation of optically active compounds and the methodology should provide information as to the scope and limitations of the intramolecular Nicholas reaction. %%% With this Research in Undergraduate Institutions award, the Synthetic Organic Program is supporting the research of Dr. David D. Grove of the Department of Chemistry at Eckard College. Professor Grove will focus his work on the development of new syntheses of important compounds, the morphinans, which are related to the widely used analgesic, morphine. His research will be carried out with the aid of undergraduate colleagues. ***

9315989格罗夫研究的重点是使用分子内捕获钴稳定的炔丙基阳离子来构建关键的顺式-乙炔基八氢菲中间体。 然后使用亚胺基自由基环化附加D-环。 所得的高级中间体具有提供多种N-取代的吗啡喃的潜力。 该路线适合于制备光学活性化合物，并且该方法应提供关于分子内Nicholas反应的范围和限制的信息。 有了这个本科院校研究奖，合成有机计划支持博士的研究。大卫D。埃卡德学院化学系的格罗夫说。 格罗夫教授的工作将集中在开发新的合成的重要化合物，吗啡，这是有关广泛使用的止痛药，吗啡。 他的研究将在本科同事的帮助下进行。 ***