通过醛的 α-烷基化实现手性有机催化构建六氢吡咯并吲哚，从而全合成 (+)-gliocladin C。
Enantioselective organocatalytic construction of hexahydropyrroloindole by means of α-alkylation of aldehydes leading to the total synthesis of (+)-gliocladin C.
机构信息
Microscale Joint Laboratory of Green Synthetic Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, PR China.
出版信息
Chemistry. 2013 Mar 4;19(10):3319-23. doi: 10.1002/chem.201204522. Epub 2013 Feb 10.
12-step program: The combined use of cinchona alkaloid based amine and chiral phosphoric acid enabled the asymmetric alkylation reaction of 3-hydroxyoxindoles with aldehydes to give 3,3'-disubstituted oxindoles in excellent enantioselectivities, which allows for the enantioselective total synthesis of (+)-gliocladin C in 12 steps from 3-hydroxyoxindole with 19 % overall yield (see scheme; PMB = para-methoxybenzyl).
12 步程序：利用金鸡纳生物碱衍生的胺和手性磷酸，实现了 3-羟基吲哚与醛的不对称烷基化反应，以优异的对映选择性得到 3,3'-二取代的吲哚啉，从 3-羟基吲哚啉以 19%的总收率（见方案；PMB=对甲氧基苄基）经过 12 步可以对 (+)-gliocladin C 进行对映选择性全合成。
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