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

被引：13

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

共 50 条

[41] Synthesis and biological evaluation of fluorinated analogues of ripostatin A
Shenderman V.
Prusov E.V.
Organic and Biomolecular Chemistry, 2019, 17 (06): : 1362 - 1364
[42] Synthesis and evaluation of fluorinated antifreeze glycoprotein analogues
Chaytor, J. L.
Denis, R. C.
Ben, R. N.
BIOPOLYMERS, 2007, 88 (04) : 559 - 559
[43] Synthesis of fluorinated carbocyclic pyrimidine nucleoside analogues
Benckendorff, Caecilie M. M.
Slyusarchuk, Valentyna D.
Huang, Ningwu
Lima, Marcelo A.
Smith, Mark
Miller, Gavin J.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (47) : 9469 - 9489
[44] A convergent approach for the synthesis of fluorinated sphingosine analogues
Teare, Harriet
Huguet, Florian
Tredwell, Matthew
Thibaudeau, Sebastien
Luthra, Sajinder
Gouverneur, Veronique
ARKIVOC, 2007, : 232 - 244
[45] Synthesis and biological evaluation of fluorinated analogues of ripostatin A
Shenderman, Vladyslav
Prusov, Evgeny V.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (06) : 1362 - 1364
[46] Deoxyribonolactone lesion in DNA: Synthesis of fluorinated analogues
Crey, C
Dumy, P
Lhomme, J
Kotera, M
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2003, 22 (5-8): : 1093 - 1095
[47] Synthesis and characterization of norbornanediol isomers and their fluorinated analogues
Grayson, SM
Long, BK
Kusomoto, S
Osborn, BP
Callahan, RP
Chambers, CR
Willson, CG
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 341 - 344
[48] Nucleic acid analogues: Synthesis and biomimetic reactions
Han, MJ
Chang, JY
MACROMOLECULAR SYMPOSIA, 1997, 118 : 61 - 66
[49] Synthesis of Fluorinated Cyclopropyl Amino Acid Analogues: Toward the Synthesis of Original Fluorinated Peptidomimetics.
Milanole, Gaelle
Couve-Bonnaire, Samuel
Bonfanti, Jean-Francois
Jubault, Philippe
Pannecoucke, Xavier
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (02): : 212 - 223
[50] Synthesis and acetylcholinesterase inhibitory activity of fluorinated analogues of huperzine A
Kaneko, S
Nakajima, N
Shikano, M
Katoh, T
Terashima, S
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (16) : 1927 - 1930

← 1 2 3 4 5 →