Okitsu Takashi, Nakazawa Daisuke, Nakagawa Kimie, Okano Toshio, Wada Akimori
Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Kobe 658-8558, Japan.
Chem Pharm Bull (Tokyo). 2010 Mar;58(3):418-22. doi: 10.1248/cpb.58.418.
Palladium-catalyzed cross-coupling reactions of a 2-substituted 3-iodobenzo[b]furans and stannanyl ester afforded the stereoselective production of 9Z-retinoic acid ester analogs in good yields. These esters were then converted to the corresponding acids via basic hydrolysis in excellent yields, and their biological activities were evaluated. The analog changed the connected position of polyene side chain from 2-position to 3-position of benzo[b]furan decreased the biological activities dramatically, and the introduction of various substituents at 2-position afforded almost no effect on the activities.
2-取代的3-碘苯并[b]呋喃与锡烷基酯的钯催化交叉偶联反应以良好的产率立体选择性地生成了9Z-视黄酸酯类似物。然后通过碱性水解将这些酯以优异的产率转化为相应的酸，并对其生物活性进行了评估。该类似物将多烯侧链的连接位置从苯并[b]呋喃的2-位改变为3-位，显著降低了生物活性，并且在2-位引入各种取代基对活性几乎没有影响。
