ALKYNYLIODONIUM SALTS IN ORGANIC SYNTHESIS

有机合成中的炔基碘盐

基本信息

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
项目类别：
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

项目摘要

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：（逐字从申请人的摘要中）继续酸性盐盐介导的碳环粒化和开发杂环的反应，并将这种化学的应用于总计计划综合治疗上有希望的天然产品。简洁 Menispermaceae的有效抗白血病原理的合成，将启动pareitropone。此外，综合程序指示朝着结构新颖的VCAM-1诱导抑制剂Halichlorine将开始。发现由亲核触发的新级联自动化的发现除了适当定位不饱和的炔烃盐盐功能将构成拟议研究的中心作用。这些多步转换将导致各种各样的有效组装通常遇到的多环形系统，包括diquinanes，前旋转前，α-甲基环戊烯酮，环旋转的苯并呋喃，和环旋转的吲哚。在另一个方面，一代和甲己二氧基甲基碳烯的生产性卡旋转将是调查。这些发展研究的前进将是其次是将方法应用于同源的合成目标。综上所述，这些研究将引入新的简洁制备小型多环子有机分子的技术类型通常是作为药物导管而寻求的。