Organic Chemistry: Multistep Synthesis, New Synthetic Methodology, Exploratory Chemistry

有机化学：多步合成、新合成方法、探索化学

• 批准号: 9811917
• 负责人: Elias Corey
• 金额: $ 81万
• 依托单位: Harvard University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 1998
• 资助国家: 美国
• 起止时间: 1998-07-15 至 2002-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=9811917&HistoricalAwards=false
• 关键词: Organic; Chemistry; Multistep; Synthesis; New

The foci of this research extend to total synthesis and methodology development. Specific molecular targets include the TNF-alpha antagonist vinigrol, the potent insecticidal alkaloid haplophytine, the octacyclic polyterpenoid octacyclononaprenol, the plant hormone precursor 3alpha-hydroxy-ent-kaurene and the potent steroidal contraceptive agent desogestrel. Among the topics of study in new methodology are enantioselective catalytic phase transfer alkylation of enolates, design and application of chiral super Lewis acids as catalysts for enantioselective synthesis, new oxazaborolidine catalysts for the enantioselective reduction of carbonyl groups, a new process for the synthesis of chiral alpha-stannyl- and alpha-lithio-carbinols, and new stereospecific methods for the synthesis of olefins by fragment coupling and the application of theses products to the synthesis of complex polycyclic structures by cation-olefin cyclization. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Elias J. Corey of the Department of Chemistry and Chemical Biology at Harvard University. Professor Corey will focus his work on the development of multistep synthetic pathways to complex, bioactive organic compounds and on the discovery of new and general methods for the construction of organic molecules.

这项研究的重点延伸到全面综合和方法论的发展。特定的分子靶点包括肿瘤坏死因子-α拮抗剂长春花酚、有效的杀虫生物碱单叶藻素、八环多烯类八环芳香酚、植物激素前体3α-羟基对甲苯磺酸和有效的类固醇避孕剂地格孕酮。在新方法学方面的研究课题包括：烯醇酸酯的对映体选择性催化相转移烷基化反应，手性超级Lewis酸作为对映体选择性合成催化剂的设计和应用，恶唑硼烷对映体选择性还原的新催化剂，手性α-锡基和α-锂硫代甲醇的合成新工艺，以及通过片段偶联合成烯烃的立体定向新方法，以及这些产品在阳离子-烯烃环化合成复杂多环结构中的应用。通过这一续展奖项，有机和高分子化学项目支持哈佛大学化学和化学生物学系的Elias J.Corey博士的研究。科里教授将专注于开发合成复杂的生物活性有机化合物的多步骤合成途径，并发现构建有机分子的新的通用方法。