Synthesis of 2′,3′-cyclohexen bicyclic uridine analogues using ring-closure metathesis

被引：6

作者：

Drone, Jullien

Egorov, Maxim

Hatton, Wilfried

Bertrand, Marie-Jo

Len, Christophe

Lebreton, Jacques

机构：

[1] Univ Nantes, CNRS, UMR 6513, Synth Organ Lab, F-44322 Nantes 3, France

[2] Univ Poitiers, CNRS, UMR 6514, FR 2703, F-86022 Poitiers, France

来源：

SYNLETT | 2006年 / 09期

关键词：

antivirals; nucleic acid analogues; radical allylation; ring-closure metathesis;

D O I：

10.1055/s-2006-941568

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of two new 2',3'-cyclohexen bicyclic uridine analogues is described. From 5'-protected uridine two successive tin radical-mediated allylations at 2'-C and 3'-C position followed by ring-closure olefin metathesis on the diene intermediate using Grubbs' catalyst led to the formation of the six-membered ring.

引用

页码：1339 / 1342

页数：4

共 50 条

[1] Synthesis of 4′-C,3′-O bicyclic thymidine analogues using ring closure metathesis
Montembault, M
Bourgougnon, N
Lebreton, J
TETRAHEDRON LETTERS, 2002, 43 (45) : 8091 - 8094
[2] Synthesis of 2′-O,3′-O bicyclic adenosine analogues using ring closing metathesis
Busca, P
Etheve-Quelquejeu, M
Valéry, JM
TETRAHEDRON LETTERS, 2003, 44 (51) : 9131 - 9134
[3] Synthesis of Cyclic Polystyrenes Using Living Anionic Polymerization and Metathesis Ring-Closure
Quirk, Roderic P.
Wang, Shih-Fan
Foster, Mark D.
Wesdemiotis, Chrys
Yol, Aleer M.
MACROMOLECULES, 2011, 44 (19) : 7538 - 7545
[4] Synthesis of chiral bicyclic lactams using ring closure metathesis: Synthesis of (-)-coniceine and (S)-pyrrolam A
Arisawa, M
Takezawa, E
Nishida, A
Mori, M
Nakagawa, M
SYNLETT, 1997, (10) : 1179 - &
[5] Enantioselective syntheses of L-carbanucleosides, using ring-closure metathesis
Agrofoglio, LA
Amblard, F
Charamon, S
Gillaizeau, I
ANTIVIRAL RESEARCH, 2002, 53 (03) : A48 - A48
[6] FORMATION OF SOME BICYCLIC SYSTEMS BY RADICAL RING-CLOSURE
BECKWITH, ALJ
PHILLIPOU, G
SERELIS, AK
TETRAHEDRON LETTERS, 1981, 22 (29) : 2811 - 2814
[7] SYNTHESIS OF THE BICYCLIC MOIETY OF THE MIHARAMYCINS BY SAMARIUM(II) IODIDE INDUCED RING-CLOSURE
FAIRBANKS, AJ
SINAY, P
SYNLETT, 1995, (03) : 277 - 279
[8] Benzoporphyrins via an olefin ring-closure metathesis methodology
Jiao, Lijuan
Hao, Erhong
Fronczek, Frank R.
Vicente, M. Graca H.
Smith, Kevin M.
CHEMICAL COMMUNICATIONS, 2006, (37) : 3900 - 3902
[9] Ring-closure metathesis reactions of novel ynamides.
Huang, J
Xiong, H
Hsung, RP
Grebe, T
Mulder, JA
Rameshkumar, C
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U185 - U186
[10] Asymmetric synthesis of differentially protected 2,7-diaminosuberic acid, a ring-closure metathesis approach
Williams, RM
Liu, JW
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (07): : 2130 - 2132

← 1 2 3 4 5 →