Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels-Alder reaction: Total synthesis of (－)-himbacine
Lipase-catalyzed asymmetric synthesis of naphtho[2,3-c]furan-1(3H)-one derivatives by a one-pot dynamic kinetic resolution/intramolecular Diels-Alder reaction: Total synthesis of (－)-himbacine
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脂肪酶催化一锅动态动力学拆分/分子内Diels-Alder反应不对称合成萘并[2,3-c]呋喃-1(3H)-酮衍生物：(－)-himbacine的全合成
DOI：
10.1016/j.bmc.2017.08.019
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发表时间：
2018
影响因子：
3.5
通讯作者：
Shuji Akai
中科院分区：
文献类型：
--
作者：
Koji Sugiyama;Shinji Kawanishi;Yasuhiro Oki;Marin Kamiya;Ryosuke Hanada;Masahiro Egi;Shuji Akai
一锅顺序反应使用的酰基部分安装的酶动力学拆分醇的研究很少。在这项工作中，丙烯酰基部分安装通过脂肪酶/氧钒组合催化动态动力学拆分外消旋二烯醇[4-（环己-1-烯-1-基）丁-3-烯-2-醇或1-（环己-1-烯-1-基）丁-2-烯-1-醇]与（Z）-3-（环己-1-烯-1-基）丁-2-烯-1-醇（苯磺酰基）丙烯酸酯在一锅法中进行分子内Diels-Alder反应以产生光学活性萘并[2，3-c]呋喃-1（3 H）-酮衍生物（98%ee）。该方法已成功应用于（-）-himbacine的不对称全合成。
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.