Department of Biomolecular Sciences , University of Urbino "Carlo Bo" , P.zza Rinascimento 6 , 61029 Urbino , PU , Italy.
J Org Chem. 2019 Sep 20;84(18):12221-12227. doi: 10.1021/acs.joc.9b02020. Epub 2019 Sep 6.
The concise and convergent total syntheses of (+)- and (-)-Fumimycin have been achieved by taking advantage of strategies for the asymmetric aza-Friedel-Crafts reaction of a highly substituted hydroquinone and -fumaryl ketimine generated from the corresponding dehydroalanine. The enantiomerically pure natural product and its enantiomer were prepared in seven steps and 22% overall yield by employing both enantiomers of a BINOL-derived chiral phosphoric acid (CPA) catalyst.
（+）-和（-）-Fumimycin 的简洁和会聚的全合成已经通过利用高度取代的对苯二酚的不对称氮杂-Friedel-Crafts 反应和从相应的脱羟丙氨酸生成的-fumaryl 亚胺的策略来实现。通过使用手性磷酸（CPA）催化剂的两种对映异构体，通过七个步骤和 22%的总收率制备了对映体纯的天然产物及其对映体。
