Bioorganic & Medicinal Chemistry ( IF 3.5 ) Pub Date : 2017-08-16 , DOI: 10.1016/j.bmc.2017.08.019 Koji Sugiyama , Shinji Kawanishi , Yasuhiro Oki , Marin Kamiya , Ryosuke Hanada , Masahiro Egi , Shuji Akai
One-pot sequential reactions using the acyl moieties installed by enzymatic dynamic kinetic resolution of alcohols have been little investigated. In this work, the acryloyl moiety installed via the lipase/oxovanadium combo-catalyzed dynamic kinetic resolution of a racemic dienol [4-(cyclohex-1-en-1-yl)but-3-en-2-ol or 1-(cyclohex-1-en-1-yl)but-2-en-1-ol] with a (Z)-3-(phenylsulfonyl)acrylate underwent an intramolecular Diels–Alder reaction in a one-pot procedure to produce an optically active naphtho[2,3-c]furan-1(3H)-one derivative (98% ee). This method was successfully applied to the asymmetric total synthesis of (−)-himbacine.
中文翻译:
一锅动力学动力学拆分/分子内狄尔斯-阿尔德反应的脂肪酶催化萘[2,3 - c ]呋喃-1(3 H)-one衍生物的不对称合成:(-)-himbacine的总合成
很少研究使用通过醇的酶动力学动力学拆分而安装的酰基部分的一锅顺序反应。在这项工作中,通过脂肪酶/氧钒组合催化的外消旋二烯醇[4-(cyclohex-1-en-1-yl)but-3-en-2-ol或1-( (Z)-3-(苯磺酰基)丙烯酸酯与环己基1-en-1-基)丁-2-烯-1-醇]通过一锅法进行分子内Diels-Alder反应以产生光学活性萘并[2,3 - c ]呋喃-1(3 H)-一衍生物(98%ee)。该方法已成功应用于(-)-半胱氨酸的不对称全合成。