Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline

被引：14

作者：

Giovanelli, Emerson ^{[1
]}

Moisan, Lionel ^{[1
]}

Comesse, Sebastien ^{[1
]}

Leroux, Sebastien ^{[1
]}

Rousseau, Bernard ^{[1
]}

Hellier, Paul ^{[2
]}

Nicolas, Marc ^{[2
]}

Doris, Eric ^{[1
]}

机构：

[1] CEA, iBiTecS, Serv Chim Bioorgan & Marquage, F-91191 Gif Sur Yvette, France

[2] Ctr Dev Chim Ind, Labs Pierre Fabre, F-81600 Gaillac, France

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 35期

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; VINBLASTINE-TYPE ALKALOIDS; VINCA ALKALOIDS; DIHYDROINDOLE ALKALOIDS; ALLYLIC OXIDATION; TERT-BUTYLHYDROPEROXIDE; POLONOVSKI REACTION; NATURAL-PRODUCTS; DERIVATIVES; ANHYDROVINBLASTINE;

D O I：

10.1039/c3ob41170b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of 20,20-difluorocatharanthine and congeners, starting from the naturally occurring catharanthine, are reported. The fluorinated catharanthine analogues were investigated as potential precursors to dimeric Vinca alkaloids of the vinflunine family. However, the biomimetic coupling of the fluorinated catharanthine derivatives with vindoline led to unexpected alkaloid structures, the formation of which was rationalized.

引用

页码：5885 / 5891

页数：7

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