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：（逐字来自申请人的摘要） 炔基碘鎓盐介导的碳环化反应的研究进展 杂环化反应，以及这种化学方法在全 合成有治疗前景的天然产物，计划。一个简洁 从防己科植物中合成有效的抗白血病成分， 将开始使用帕拉西酮。此外，一个合成程序直接 对于结构新颖的VCAM-1诱导抑制剂卤氯， 开始吧。亲核引发的新级联环化反应的发现 除了具有适当位置的不饱和的炔基碘鎓盐之外 功能性将构成拟议研究的中心重点。这些 多步骤转换将导致各种 通常遇到的多环体系，包括二醌， 前己内酰胺，α-亚甲基环戊酮，环戊烷化的苯并呋喃， 和环戊烷化吲哚。另一方面，这一代人和 甲硅烷基氧基亚烷基卡宾的生产性碳环化将是 研究了这些发展研究的有希望的进展将是 其次是对同源的合成方法的应用 目标的综合起来，这些研究将介绍新的和简洁的 制备多环有机小分子的技术 典型的医药领导者。