On the Elucidation of the Mechanism of Vinca Alkaloid Fluorination in Superacidic Medium

被引：17

作者：

Giovanelli, Emerson ^{[2
]}

Leroux, Sebastien ^{[2
]}

Moisan, Lionel ^{[2
]}

Carreyre, Helene ^{[3
]}

Thuery, Pierre ^{[4
]}

Buisson, David-Alexandre ^{[2
]}

Meddour, Abdelkrim ^{[5
]}

Coustard, Jean-Marie ^{[3
]}

Thibaudeau, Sebastien ^{[3
]}

Rousseau, Bernard ^{[2
]}

Nicolas, Marc ^{[1
]}

Hellier, Paul ^{[1
]}

Doris, Eric ^{[2
]}

机构：

[1] Ctr Dev Chim Ind, Lab Pierre Fabre, F-81600 Gaillac, France

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

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

[4] IRAMIS, CEA, Serv Interdisciplinaire Syst Mol & Mat, F-91191 Gif Sur Yvette, France

[5] Univ Paris 11, ICMMO, UMR 8182, F-91405 Orsay, France

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 15期

关键词：

STEREOCONTROLLED TOTAL-SYNTHESIS; DIHYDROINDOLE ALKALOIDS; ANHYDROVINBLASTINE; VINBLASTINE; DERIVATIVES; LEUROSINE; HF-SBF5; ACCESS; INDOLE; (+)-CATHARANTHINE;

D O I：

10.1021/ol201637m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20' activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments unambiguously revealed the involvement of a 1,2-hydride shift mechanism.

引用

页码：4116 / 4119

页数：4

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