ALKYNYLIODONIUM SALTS IN ORGANIC SYNTHESIS

有机合成中的炔基碘盐

• 批准号: 6385661
• 负责人: KEN S. FELDMAN
• 金额: $ 22.32万
• 依托单位: PENNSYLVANIA STATE UNIVERSITY, THE
• 依托单位国家: 美国
• 财政年份: 1987
• 资助国家: 美国
• 起止时间: 1987-01-01 至 2004-06-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/6385661
• 关键词: alkaloids; alkynes; antileukemic agent; antineoplastics; carbene; carbopolycyclic compound; chemical addition; cyclization; drug design /synthesis /production; free radicals; iodine; stereochemistry

Description: (Verbatim from the Applicant's Abstract) The continuing development of alkynyliodonium salt-mediated carbocyclization and heterocyclization reactions, and application of this chemistry to the total synthesis of therapeutically promising natural products, is planned. A concise synthesis of the potent antileukemic principle from Menispermaceae, pareitropone, will be initiated. In addition, a synthesis program directed toward the structurally novel VCAM-1 induction inhibitor halichlorine will commence. The discovery of new cascade cyclizations triggered by nucleophilic addition to alkynyliodonium salts bearing appropriately positioned unsaturated functionality will constitute a central thrust of the proposed research. These multi-step transformations will lead to efficient assembly of a variety of commonly encountered polycyclic ring systems, including diquinanes, precapnellanes, alpha-methylenecyclopentanones, cyclopentannelated benzofurans, and cyclopentannelated indoles. In a separate vein, the generation and productive carbocyclization of silyloxyalkylidene carbenes will be investigated. Promising advances in these developmental studies will be followed by application of the methodology toward the synthesis of cognate targets. Taken together, these studies will introduce new and concise techniques for preparing small polycyclic organic molecules of the type typically sought as pharmaceutical leads.

描述：(逐字摘自申请人的摘要)继续 炔基碘盐介导碳环化反应的研究进展 杂环化反应及其在总反应中的应用 正在计划合成具有治疗前景的天然产品。简明扼要 防己科有效抗白血病活性成分的合成 帕瑞特隆，将被启动。此外，一个指导的合成程序 结构新颖的VCAM-1诱导抑制剂卤代氯将 开始。亲核引发的新的级联环化反应的发现 添加具有适当位置的不饱和的烷基碘盐 功能性将构成拟议研究的中心主旨。这些 多步转换将导致高效地组装各种 常见的多环环体系，包括二喹烷， 前戊烷，α-亚甲基环戊酮，环戊烷基苯并呋喃， 和环戊烷相关的吲哚。在不同的脉络中，这一代人和 硅氧基亚烷基卡宾的生产性碳环化反应将是 调查过了。这些发展研究的有希望的进展将是 其次是方法论在同源词合成中的应用 目标。综上所述，这些研究将介绍新的和简洁的 多环有机小分子的制备技术 通常作为药物线索寻找的类型。