Le Goanvic David, Tius Marcus A
University of Hawaii, Chemistry Department, Honolulu, Hawaii 96822, USA.
J Org Chem. 2006 Sep 29;71(20):7800-4. doi: 10.1021/jo061352c.
The preparation of C3 oxaza adamantyl cannabinoids has been described starting from phloroglucinol. Straightforward manipulations of the aromatic ring lead to a bromononaflate that is a benzyne precursor and that serves as a common intermediate for the synthesis of diverse C3-substituted tricyclic cannabinoids. Generation of the benzyne in the presence of an oxaza adamantyl amide anion results in efficient and regiospecific addition to C3 of the aromatic ring. This represents an attractive strategy for the synthesis of classical tricyclic cannabinoids that bear a modified aromatic appendage. The oxaza adamantyl cannabinoids that have been prepared represent a new class of ligands for the CB1 and CB2 receptors.
已经描述了从间苯三酚开始制备C3氧杂金刚烷基大麻素的方法。对芳环进行直接操作可得到一种溴代壬氟化物，它是苯炔前体，也是合成多种C3-取代的三环大麻素的通用中间体。在氧杂金刚烷基酰胺阴离子存在下生成苯炔会导致其对芳环的C3位进行有效且区域选择性的加成。这是合成带有修饰芳基附属物的经典三环大麻素的一种有吸引力的策略。已制备的氧杂金刚烷基大麻素代表了一类新型的CB1和CB2受体配体。
