SYNTHESIS OF ANATOXIN-A

Anatoxin-A 的合成

• 批准号: 3438678
• 负责人: HAROLD W PINNICK
• 金额: $ 7.45万
• 依托单位: BUCKNELL UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1988
• 资助国家: 美国
• 起止时间: 1988-06-01 至 1990-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3438678
• 关键词: Cyanophyta; Diels Alder reaction; acetylcholine; alkaloids; drug design /synthesis /production; muscle relaxants; neural transmission; neurotoxins; nicotinic receptors; pyrroles; synapses

The major long-term objective of this project is the synthesis of anatoxin-a using chemistry which will allow large quantities to be prepared as well as numerous analogs. Initially, the carbocyclic analog will be prepared starting with the Diels-Alder adduct of cyclopentadiene and maleic anhydride. Reaction with dimethylcuprate, a Hunsdiecker reaction and loss of hydrogen bromide gives acetylnorbornene. Cycloaddition with acetylene or 1,2-dichloroethylene should give a bicyclo(4.2.1)dienone which can be reduced to the desired analog of anatoxin-a. The alkaloid itself will be prepared using similar chemistry starting from pyrrole.

该项目的主要长期目标是综合 Anatoxin-一种使用化学的方法，将允许大量的 准备了大量的类似物。最初，碳环 类似物将从Diels-Alder加合物开始制备 环戊二烯和顺丁烯二酸酐。反应与 铜酸二甲酯、Hunsdiecker反应和氢的损失 溴化物产生乙酰降冰片烯。与乙炔的环加成反应 1，2-二氯乙烯应该生成双环(4.2.1)二烯酮，它可以 被还原为所需的Anatoxin-a类似物。生物碱 本身将使用类似的化学方法制备，从 吡咯。