Functionalization of a non activated C-H bond: Fluorination of vindoline at C-20 in superacids

被引：14

作者：

Berrier, C

Jacquesy, JC

Jouannetaud, MP

Lafitte, C

Vidal, Y

Zunino, F

Fahy, J

Duflos, A

机构：

[1] Univ Poitiers, Lab Synth & Reactiv Substances Nat, UMR 6514, F-86022 Poitiers, France

[2] Ctr Rech Pierre Fabre, Div Chim Med 5, F-81106 Castres, France

来源：

TETRAHEDRON | 1998年 / 54卷 / 45期

关键词：

D O I：

10.1016/S0040-4020(98)00845-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of vindoline 1a with NBS, NCS, H2O2 in HF-SbF5 yields 7 beta substituted (Br, Cl or OH)-20-fluoro-6,7-dihydrovindolines. These results imply reaction of the electrophile (Br+, Cl+ and OH+ equivalent) on the beta-face of C-6-C-7 double bond to give oniums ions, followed by a 1,3-hydride shift from C-20 to Cd, and fluorination of the resulting ion. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：13761 / 13770

页数：10

共 14 条

[1]

[Anonymous], ALKALOIDS ANTITUMOR

[2] SYNTHESIS OF FLUOROHYDRINS AND OF BROMOFLUORODERIVATIVES BY ANTI ADDITION ON THE 14,15 DOUBLE-BOND OF TABERSONINE IN SUPERACIDS [J].