Online citations, reference lists, and bibliographies.
← Back to Search

One-Pot Conversion Of Proline Derivatives Into Iodinated Iminosugar-Based Nucleosides, Useful Precursors Of Highly Functionalized Nucleoside Analogues

A. Boto, D. Hernández, R. Hernández
Published 2010 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Readily available proline derivatives can be transformed in one step into β-iodinated iminosugar-based nucleosides, under very mild conditions. The method couples a tandem radical decarboxylation-oxidation-β-iodination to the addition of nitrogen bases. The iodo group is introduced into the previously unfunctionalized 3-position. The resultant β-iodo derivatives are useful precursors of highly functionalized nucleoside analogues.
This paper references
10.1021/cr900169j
Synthesis of cyclopentitols by ring-closing approaches.
V. Kurteva (2009)
10.1002/CHIN.200730227
Modification of Amino Acids, Peptides, and Carbohydrates Through Radical Chemistry
S. Hansen (2006)
10.1016/S0040-4039(99)00151-3
HECK REACTION OF ENDOCYCLIC ENECARBAMATES WITH DIAZONIUM SALTS. FORMAL ENANTIOSELECTIVE SYNTHESES OF ALKALOIDS (-)-CODONOPSINE AND (-)-CODONOPSININE, AND THE SYNTHESIS OF A NEW C-ARYL AZASUGAR
D. F. Oliveira (1999)
10.1021/jo901604w
An efficient route to acyclic C-nucleosides and fused-ring analogues of uridine from exo-glycals.
Gérald Enderlin (2009)
10.1016/J.BMCL.2006.10.070
Synthesis and DNA-binding ability of C2R-fluoro substituted DC-81 and its dimers.
A. Kamal (2007)
10.1016/S1567-5769(01)00056-X
Purine nucleoside phosphorylase inhibitor BCX-1777 (Immucillin-H)--a novel potent and orally active immunosuppressive agent.
S. Bantia (2001)
10.1016/J.JFLUCHEM.2008.02.008
Synthesis of 2′,3′-dideoxy-6′,6′-difluoro-3′-azanucleosides
Xuyi Yue (2008)
10.1016/J.TETLET.2007.11.113
One-pot synthesis of azanucleosides from proline derivatives
A. Boto (2008)
10.1016/j.bmcl.2008.08.047
Immucillins in custom catalytic-site cavities.
A. S. Murkin (2008)
10.1021/jo902313g
A general and efficient synthesis of pyridin-2-yl C-ribonucleosides bearing diverse alkyl, aryl, amino, and carbamoyl groups in position 6.
Martin Štefko (2010)
10.1016/j.tetlet.2009.04.082
Enantiopure alkaloid analogues and iminosugars from proline derivatives: stereocontrol in sequential processes
Alicia Boto (2009)
10.1021/JM900932G
Highlights in the discovery of antiviral drugs: a personal retrospective.
E. Clercq (2010)
10.1055/S-0029-1218539
Asymmetric BrønstedAcid Catalyzed Nucleophilic Addition to in situ GeneratedChiral N-Acyliminium Ions
M. Rueping (2010)
10.1039/b913066g
1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents.
C. Nájera (2009)
10.1021/jm900197j
Stereoselective synthesis and biological evaluations of novel 3'-deoxy-4'-azaribonucleosides as inhibitors of hepatitis C virus RNA replication.
U. Chiacchio (2009)
10.1021/cr900028p
Enzymology of purine and pyrimidine antimetabolites used in the treatment of cancer.
W. Parker (2009)
10.1021/CR050528S
Alpha-amido sulfones as stable precursors of reactive N-acylimino derivatives.
M. Petrini (2005)
10.1021/JA993366O
Stereochemical Reversal of Nucleophilic Substitution Reactions Depending upon Substituent: Reactions of Heteroatom-Substituted Six-Membered-Ring Oxocarbenium Ions through Pseudoaxial Conformers
J. Romero (2000)
10.1021/JO0107958
Simple entry to 3'-substituted analogues of anti-HIV agent stavudine based on an anionic O --> C stannyl migration.
H. Kumamoto (2002)
10.1016/J.TET.2008.11.035
Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues
V. Vaněk (2009)
10.1021/JM030455+
Synthesis of a potent transition-state inhibitor of 5'-deoxy-5'-methylthioadenosine phosphorylase.
V. Kamath (2004)
10.1002/EJOC.201000360
One-Pot Synthesis of Azanucleosides from Proline Derivatives -Stereoselectivity in Sequential Processes
A. Boto (2010)
10.1002/CHIN.199651239
Some recent trends and progress in nucleoside synthesis.
H. Vorbrueggen (1996)
10.1016/S0040-4039(00)02343-1
Stereoselective synthesis of azanucleosides aza-stavudine (aza-D4T), aza-2′,3′-didehydro-3′-deoxyuridine (aza-D4U), and its hydrogenated analogues from an endocyclic enecarbamate
E. R. Costenaro (2001)
10.1016/J.TET.2006.03.078
Synthesis of racemic and enantiomeric 3-pyrrolidinyl derivatives of nucleobases
Petr Kočalka (2006)
10.1016/J.TETLET.2006.10.007
One-pot synthesis of β-amino acid derivatives from α-amino acids
Carlos J Saavedra (2006)
10.1016/J.TET.2006.11.076
Recent developments in asymmetric catalytic addition to CN bonds
G. K. Friestad (2007)
10.1021/OL0161054
Short, highly efficient syntheses of protected 3-azido- and 4-azidoproline and their precursors.
J. A. Gómez-Vidal (2001)
10.1021/cr9002165
C-nucleosides: synthetic strategies and biological applications.
J. Štambaský (2009)
10.1021/jo9004487
Catalytic, one-pot synthesis of beta-amino acids from alpha-amino acids. Preparation of alpha,beta-peptide derivatives.
Carlos J Saavedra (2009)
10.1021/JA064682N
O6-(benzotriazol-1-yl)inosine derivatives: easily synthesized, reactive nucleosides.
Suyeal Bae (2007)
10.1055/S-2006-958957
Recent Advances in Stereoselective Syntheses Using N-Acylimines
M. Petrini (2007)
10.1021/CR0306182
Cyclizations of N-acyliminium ions.
B. Maryanoff (2004)
10.1021/ol902142w
Microwave-assisted synthesis of 2'-O-aryluridine derivatives.
Yusuke Oeda (2009)
10.1016/J.TET.2006.11.047
Synthesis of diastereomeric 3-hydroxy-4-pyrrolidinyl derivatives of nucleobases
D. Rejman (2007)
10.1016/J.BMCL.2007.01.034
Studies on acyl pyrrolidine inhibitors of HCV RNA-dependent RNA polymerase to identify a molecule with replicon antiviral activity.
G. Burton (2007)
10.1021/OL070412D
Short and efficient synthesis of chiral furyl carbinols from carbohydrates.
A. Boto (2007)
10.1016/J.TET.2007.06.043
Catalytic, asymmetric alkylation of imines
D. Ferraris (2007)
10.1021/CR020083X
Chiral heterocycles by iminium ion cyclization.
J. Royer (2004)
10.1002/EJOC.200600720
Synthesis of Alkaloid Analogues from β‐Amino Alcohols by β‐Fragmentation of Primary Alkoxyl Radicals
A. Boto (2007)
10.1021/jm800927r
Discovery of novel arylethynyltriazole ribonucleosides with selective and effective antiviral and antiproliferative activity.
Jinqiao Wan (2009)
10.1002/EJOC.200400698
Synthesis of Functionalized Nitrogen Heterocycles by Radical Decarboxylation of β- and γ-Amino Acids
A. Boto (2005)
10.1016/J.TETLET.2004.08.167
Chemoenzymatic synthesis of (3 S,4 S)- and (3 R,4 R)-3-methoxy-4-methylaminopyrrolidine
A. Kamal (2004)
10.1021/ja902679b
Influence of biaryl phosphine structure on C-N and C-C bond formation.
R. Pratap (2009)
10.1021/cr800332c
Chemistry of polyvalent iodine.
Viktor V. Zhdankin (2008)
10.1021/cr9001462
Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry.
F. Amblard (2009)
10.1021/JO701608P
One-pot synthesis of acyclic nucleosides from carbohydrate derivatives, by combination of tandem and sequential reactions.
A. Boto (2007)
10.1016/j.bmc.2009.04.054
Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain
Mariola Koszytkowska-Stawińska (2009)
10.1016/S0040-4020(97)10352-0
SYNTHESIS OF (2S, 3R, 4S), (2S, 3S, 4R)-EPOXYPROLINES AND AMINOHYDROXYPROLINES
J. Robinson (1998)
10.1021/JA068589A
Reactions of a N-acyliminium ion pool with benzylsilanes. Implication of a radical/cation/radical cation chain mechanism involving oxidative C-Si bond cleavage.
T. Maruyama (2007)
10.1016/S0040-4020(00)00031-4
Chemoenzymatic Synthesis of Optically Active 2-Phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
D. S. Im (2000)
10.1021/JO000356T
Tandem radical decarboxylation-oxidation of amino acids: A mild and efficient method for the generation of N-acyliminium ions and their nucleophilic trapping
Boto (2000)
10.1021/JA071087S
Acyclic ribooxacarbenium ion mimics as transition state analogues of human and malarial purine nucleoside phosphorylases.
E. A. Taylor (2007)
10.1016/S0040-4039(00)76729-3
Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine
G. Rassu (1994)
10.1021/JO015877A
Synthesis of 2,3-disubstituted pyrrolidines and piperidines via one-pot oxidative decarboxylation-beta-iodination of amino acids.
A. Boto (2001)
10.1021/OL0500620
Investigations into the role of ion pairing in reactions of heteroatom-substituted cyclic oxocarbenium ions.
Siddhartha R Shenoy (2005)
10.1021/OL016970O
Novel cyclic sugar imines: carbohydrate mimics and easily elaborated scaffolds for aza-sugars.
B. Davis (2002)
10.1016/j.bmc.2008.10.063
Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library.
En-Lun Tsou (2008)
10.1002/ANIE.199416541
Synthesis of an Azathymidine and Its Incorporation into Oligonucleotides
K. Altmann (1994)
10.1039/B600056H
Electrostatic interactions in cations and their importance in biology and chemistry.
D. M. Smith (2006)
10.1016/S0040-4020(02)01020-7
Simple and efficient syntheses of Boc- and Fmoc-protected 4( R )- and 4( S )-fluoroproline solely from 4( R )-hydroxyproline
M. Doi (2002)
10.1016/j.bmc.2008.05.056
N-Arylmethyl substituted iminoribitol derivatives as inhibitors of a purine specific nucleoside hydrolase.
A. Goeminne (2008)
10.1021/CR000446Y
Biocatalytic selective modifications of conventional nucleosides, carbocyclic nucleosides, and C-nucleosides.
M. Ferrero (2000)
10.1016/J.TET.2009.06.067
Highly stereoselective synthesis of novel cyclobutane-fused azanucleosides
R. Flores (2009)
10.1002/EJOC.200800340
The Effect of Lewis Acids on the Stereochemistry in the Ugi Three-Component Reaction with D-lyxo-Pyrroline†
K. M. Bonger (2008)
10.2174/1568026033452465
Imino-sugar-based nucleosides.
V. Schramm (2003)
10.1021/jm801421q
Third-generation immucillins: syntheses and bioactivities of acyclic immucillin inhibitors of human purine nucleoside phosphorylase.
K. Clinch (2009)
10.1021/JA0524043
Stereoselective C-glycosylation reactions of ribose derivatives: electronic effects of five-membered ring oxocarbenium ions.
Catharine H. Larsen (2005)
10.1021/JA993349Z
A Stereoelectronic Model To Explain the Highly Stereoselective Reactions of Nucleophiles with Five-Membered-Ring Oxocarbenium Ions
Catharine H. Larsen (1999)
10.1039/A900800D
The synthesis of novel 3′,5′-homocyclic nucleotides as potential anti-HIV agents
M. Drew (1999)
10.1055/S-1999-3559
Synthesis and Biological Activity of Azanucleosides
M. Yokoyama (1999)
10.1021/cr900329y
Preparation of cyclonucleosides.
Adam Mieczkowski (2010)
10.1021/JO0705115
Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization Utilizing the Sonogashira Coupling Reaction in the Enantioselective Synthesis of α-Substituted β-Amino Acids
Blanca R. Díaz-Sánchez (2007)
10.1021/JA070274N
Small-molecule inhibitors of protein geranylgeranyltransferase type I.
Sabrina Castellano (2007)
10.1021/ja00386a039
An efficient stereospecific total synthesis of (.+-.)-anisomycin and related new synthetic antibiotics
D. Schumacher (1982)
Comprar Modified Nucleosides: in Biochemistry, Biotechnology and Medicine | Piet Herdewijn | 9783527318209 | Wiley
Piet Herdewijn (2008)
10.1021/ol9007475
Suzuki-miyaura and sonogashira coupling of 6-chloropurines and -nucleosides in water.
Jan Pschierer (2009)
10.1021/JM970439A
Synthesis and biological properties of new constrained CCK-B antagonists: discrimination of two affinity states of the CCK-B receptor on transfected CHO cells.
B. Bellier (1997)
10.1021/JA037935A
Stereochemistry of nucleophilic substitution reactions depending upon substituent: evidence for electrostatic stabilization of pseudoaxial conformers of oxocarbenium ions by heteroatom substituents.
Leticia Ayala (2003)
10.1021/JA0375176
Nucleophilic additions to fused bicyclic five-membered ring oxocarbenium ions: evidence for preferential attack on the inside face.
D. M. Smith (2003)
10.1016/J.BMCL.2005.06.020
Developing microcolin A analogs as biological probes.
Amit K. Mandal (2005)
10.1016/J.TETLET.2005.09.019
One-pot synthesis of α-amino phosphonates from α-amino acids and β-amino alcohols
A. Boto (2005)
10.1021/JO035744K
Imino-C-nucleoside synthesis: heteroaryl lithium carbanion additions to a carbohydrate cyclic imine and nitrone.
G. B. Evans (2004)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar