Chiral Vinyloxiranes as Synthetic Intermediates

作为合成中间体的手性乙烯基环氧乙烷

• 批准号: 8912745
• 负责人: James Marshall
• 金额: $ 27.42万
• 依托单位: University of South Carolina at Columbia
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1990
• 资助国家: 美国
• 起止时间: 1990-01-01 至 1993-06-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=8912745&HistoricalAwards=false
• 关键词: Chiral; Vinyloxiranes; Synthetic; Intermediates

The Organic Synthesis Program is funding a continuation of the research of Dr. James A. Marshall. Dr. Marshall will continue his development of new ways to control the stereochemistry in the synthesis of complex systems. These will provide the new tools required by the increasing complexity of the compounds needed by our agriculture and industry. The research will explore the scope of reactions in which nonracemic vinyloxiranes serve as key intermediates for the synthesis of subunits found in various polypropionate and related natural products. The experiments are designed to reveal intrinsic steric preferences and explore the role of directing groups in these reactions. A variety of nucleophilic reagents will be tested including nonracemic cuprates and allylmetallic compounds. By the proper selection of double bond geometry, epoxide stereochemistry and reagent sterochemistry it should be possible to exercise considerable control over the formation of multiple stereocenters. Methodology will also be explored for transforming the products of the foregoing reactions into natural products and analogs with potential antitumor, antibiotic, and immunosuppressive properties.

有机合成计划正在资助詹姆斯·A·马歇尔博士研究的继续。马歇尔博士将继续开发新的方法来控制复杂系统合成中的立体化学。这些将提供我们的农业和工业所需的化合物日益复杂所需的新工具。这项研究将探索非外消旋聚氧乙烯氧烷作为合成各种聚丙酸酯和相关天然产物中的亚基的关键中间体的反应范围。这些实验旨在揭示内在的空间偏好，并探索导向基团在这些反应中的作用。将测试各种亲核试剂，包括非外消旋铜酸盐和烯丙基金属化合物。通过选择合适的双键构型、环氧化物立体化学和试剂立体化学，应该可以对多个立体中心的形成进行相当大的控制。还将探索将上述反应产物转化为具有潜在抗肿瘤、抗生素和免疫抑制特性的天然产品和类似物的方法。