Concise and Convergent Enantioselective Total Syntheses of (+)-and (-)-Fumimycin

被引：18

作者：

Retini, Michele ^{[1
]}

Bartolucci, Silvia ^{[1
]}

Bartoccini, Francesca ^{[1
]}

Mari, Michele ^{[1
]}

Piersanti, Giovanni ^{[1
]}

机构：

[1] Univ Urbino Carlo Bo, Dept Biomol Sci, Pzza Rinascimento 6, I-61029 Urbino, PU, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 18期

关键词：

FRIEDEL-CRAFTS ALKYLATION; BRONSTED ACID CATALYSIS; DERIVATIVES; FUMIMYCIN; INDOLES;

D O I：

10.1021/acs.joc.9b02020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 N-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.

引用

页码：12221 / 12227

页数：7

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