SYNTHESIS OF DELTA-1-TETRAHYDROCANNABINOL-7-OIC ACID

Delta-1-四氢大麻酚-7-油酸的合成

• 批准号: 3424154
• 负责人: HAROLD W PINNICK
• 金额: $ 6.47万
• 依托单位: BUCKNELL UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 1990
• 资助国家: 美国
• 起止时间: 1990-09-30 至 1992-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/3424154
• 关键词: Diels Alder reaction; cannabinoids; drug design /synthesis /production; marijuana abuse

The major long-term objective of this project is the synthesis of the major metabolite of delta-l-tetrahydrocannabinol and various analogs. The route to be investigated uses dienes prepared by a Wittig reaction from phosphonium salts derived from 2,3-dihalopropenes for a Diels-Alder reaction to prepare the key vinyl halide intermediate. This compound is then converted into the appropriate dihydropyran cannabinoid skeleton using trimethylailyl iodide, chemistry which was discovered in an earlier synthesis of the primary cannabinoids. The synthesis is completed by carboxylation of the vinyl halide via an organometallic reagent.

该项目的主要长期目标是综合 德尔塔-L-四氢大麻酚及其类似物的主要代谢产物。这个 要研究的路线使用由Wittig反应制备的二烯 用于Diels-Alder的2，3-二卤丙烯衍生的膦盐 反应制备关键的卤化乙烯中间体。这种化合物是 然后转化成合适的二氢吡喃大麻碱骨架 使用三甲基碘化物，在早期发现的化学 初级大麻素的合成。合成由以下步骤完成 通过有机金属试剂使卤化乙烯发生羧化反应。