VERSATILE SYNTHESIS OF ANNONACEOUS ACETOGENINS

甘草苷的多功能合成

• 批准号: 2522509
• 负责人: BRIAN A JOHNS
• 金额: $ 2.5万
• 依托单位: UNIVERSITY OF VIRGINIA
• 依托单位国家: 美国
• 财政年份: 1998
• 资助国家: 美国
• 起止时间: 1998-06-11 至
• 项目状态: 未结题
• 来源: https://reporter.nih.gov/project-details/2522509
• 关键词: antineoplastics; butyrolactone; chemical synthesis; cyclization; plant extracts

Annonaceous acetogenins are a rapidly growing class of natural products with a vast array of biological activities including anti-tumor and pesticidal promise. This proposal describes a versatile synthetic strategy using catalytic ring closing metathesis (RCM) for accessing several adjacent bis-THF containing Annonaceous acetogenins. The use of RCM is extended to the synthesis of both the tetrahydrofuran segment as well as the butenolide terminus common to many of the acetogenins as well as a host of other natural and unnatural targets. The outlined proposal presents alternative protocols that deal with both symmetrical bis-THF core structures as well as those lacking complete symmetry. A complete proposed synthesis of a model target asimicin is presented.

番荔枝内酯是一类增长迅速的天然产物 具有广泛的生物活性，包括抗肿瘤和 农药承诺该提案描述了一种通用的合成策略 使用催化闭环复分解（RCM）来获得几种 含有番荔枝内酯的相邻双-THF。使用RCM是 扩展到合成四氢呋喃链段以及 许多乙酸配基共有的丁烯二酰末端以及 其他自然和非自然的目标。概述的提案 提出了处理对称双四氢呋喃的替代方案 核心结构以及那些缺乏完全对称性的结构。一个完整 提出了一种模型目标阿西米星的合成方法。