"CO" as a Carbon Bridge to Build Complex C2-Branched Glycosides Using a Palladium-Catalyzed Carbonylative Suzuki-Miyaura Reaction from 2-Iodoglycals

被引：29
作者：
de Robichon, Morgane [1 ]
Bordessa, Andrea [1 ]
Lubin-Germain, Nadege [1 ]
Ferry, Angelique [1 ]
机构：
[1] Univ Cergy Pontoise, LCB, EA 4505,5 Mail Gay Lussac, F-95031 Cergy Pontoise, France
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 06期
关键词：
CROSS-COUPLING REACTION; ARYL HALIDES; BIOLOGICAL EVALUATION; BENZOPYRAN COMPOUNDS; IODONIUM SALTS; GLYCALS; ANALOGS; ACCESS; FUNCTIONALIZATION; DERIVATIVES;
D O I：
10.1021/acs.joc.8b03248
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Development of a palladium-catalyzed carbonylative Suzuki-Miyaura coupling reaction between 2-iodoglycal partners and diverse aryl- and alkenyl-boronic acids is presented, leading to original 2-ketoglycals. The newly formed carbonyl link could be exploited to access 2-aryl/alkenyl-methylene-alpha-glucopyranoside scaffolds via a three-step sequence including an indium-mediated Ferrier-type reaction.
引用
收藏
页码：3328 / 3339
页数：12
相关论文
共 83 条
[1]   Structural Modifications of cis-Glycofused Benzopyran Compounds and Their Influence on the Binding to Amyloid- βPeptide [J].
Airoldi, Cristina ;
D'Orazio, Giuseppe ;
Richichi, Barbara ;
Guzzi, Cinzia ;
Baldoneschi, Veronica ;
Colombo, Laura ;
Salmona, Mario ;
Nativi, Cristina ;
Nicotra, Francesco ;
La Ferla, Barbara .
CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (02) :299-309
[2]   Nanoliposomes presenting on surface a cis-glycofused benzopyran compound display binding affinity and aggregation inhibition ability towards Amyloid β1-42 peptide [J].
Airoldi, Cristina ;
Mourtas, Spyridon ;
Cardona, Francisco ;
Zona, Cristiano ;
Sironi, Erika ;
D'Orazio, Giuseppe ;
Markoutsa, Eleni ;
Nicotra, Francesco ;
Antimisiaris, Sophia G. ;
La Ferla, Barbara .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 :43-50
[3]   Fluorescent amyloid β-peptide ligand derivatives as potential diagnostic tools for Alzheimer's disease [J].
Airoldi, Cristina ;
Cardona, Francisco ;
Sironi, Erika ;
Colombo, Laura ;
Salmona, Mario ;
Cambianica, Ilaria ;
Ornaghi, Francesca ;
Sancini, Giulio ;
Nicotra, Francesco ;
La Ferla, Barbara .
PURE AND APPLIED CHEMISTRY, 2013, 85 (09) :1813-1823
[4]   cis-Glyco-fused benzopyran compounds as new amyloid-β peptide ligands [J].
Airoldi, Cristina ;
Cardona, Francisco ;
Sironi, Erika ;
Colombo, Laura ;
Salmona, Mario ;
Silva, Artur ;
Nicotra, Francesco ;
La Ferla, Barbara .
CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10266-10268
[5]   Synthesis of (1 → 2)-S-Linked Saccharides and S -Linked Glycoconjugates via a Palladium-G3-XantPhos Precatalyst Catalysis [J].
AL-Shuaeeb, Riyadh Ahmed Atto ;
Montoir, David ;
Alami, Mouad ;
Messaoudi, Samir .
JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (13) :6720-6728
[6]   Expedient carbonylation of aryl halides in aqueous or neat condition [J].
Ang, Wei Jie ;
Lo, Lee-Chiang ;
Lam, Yulin .
TETRAHEDRON, 2014, 70 (45) :8545-8558
[7]  
[Anonymous], 2013, Green Sustain. Chem.
[8]  
Ansari AA, 2013, J ORG CHEM, V78, P9383, DOI [10.1021/jo401631v, 10.1021/jo401613v]
[9]   Synthesis and Structure-Activity Relationships of Constrained Heterocyclic Analogues of Combretastatin A4 [J].
Arthuis, Martin ;
Pontikis, Renee ;
Chabot, Guy G. ;
Seguin, Johanne ;
Quentin, Lionel ;
Bourg, Stephane ;
Morin-Allory, Luc ;
Florent, Jean-Claude .
CHEMMEDCHEM, 2011, 6 (09) :1693-1705
[10]   Palladium-Catalyzed Direct Cross-Coupling Reaction of Glycals with Activated Alkenes [J].
Bai, Yaguang ;
Zeng, Jing ;
Cai, Shuting ;
Liu, Xue-Wei .
ORGANIC LETTERS, 2011, 13 (16) :4394-4397
123456789