Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamadaoka, Suita, Osaka 567-0871, Japan.
School of Pharmaceutical Sciences, University of Shizuoka, 52-1, Yada, Suruga-ku, Shizuoka, Shizuoka 422-8526, Japan.
Bioorg Med Chem. 2018 Apr 1;26(7):1378-1386. doi: 10.1016/j.bmc.2017.08.019. Epub 2017 Aug 16.
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.
一锅法连续反应利用酶促动态动力学拆分醇中的酰基部分研究较少。在这项工作中，通过脂肪酶/氧钒配合物催化的外消旋二烯醇[4-（环己-1-烯-1-基）-3-丁烯-2-醇或 1-（环己-1-烯-1-基）-2-丁烯-1-醇]的动态动力学拆分，在一锅法中，丙烯酰基部分发生分子内 Diels-Alder 反应，生成光学活性萘[2,3-c]呋喃-1（3H）-酮衍生物（98%ee）。该方法成功应用于（-）-himbacine 的不对称全合成。
