Razdan R K, Dalzell H C, Herlihy P, Howes J F
J Med Chem. 1976 Nov;19(11):1328-30. doi: 10.1021/jm00233a014.
Two delta8-THC derivatives, 4a and 4b, with functionalized side chains were synthesized. Treatment of (+)-trans-p-mentha-2,8-dien-1-ol with the resorcinal 2b followed by removal of the dithiol group with HgO--BF3-Et2O gave the aldehyde 3b. A Wittig reaction of dimethyl (2-oxoheptyl)phosphate with 3b furnished 4a, which was reduced to 4b. Compounds 4a and 4b showed potent cannabinoid-like activity in mice.
合成了两种带有官能化侧链的δ8-四氢大麻酚衍生物4a和4b。将(+)-反式-对薄荷-2,8-二烯-1-醇与间苯二酚2b反应，然后用HgO--BF3-Et2O除去二硫醇基团，得到醛3b。磷酸二甲基(2-氧代庚基)酯与3b发生维蒂希反应得到4a，4a再被还原为4b。化合物4a和4b在小鼠中显示出强效的类大麻素活性。
