201472-26-6Relevant articles and documents
Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction
Ghosh, Arun K.,Kass, Jorden
supporting information; experimental part, p. 1218 - 1220 (2010/06/15)
We have developed a practical synthesis of unique nucleoside derivatives via TiCl4 promoted multicomponent reaction of optically active dihydrofuran, ethyl pyruvate/glyoxylate, and a TMS protected nucleobase in a single-pot operation.
A concise asymmetric synthesis of (+)-muscarine from (S)-γ-hydroxymethyl-γ-butyrolactone
Boukouvalas, John,Radu, Ioan-Iosif
, p. 2971 - 2973 (2008/02/04)
A highly stereoselective synthesis of (+)-muscarine iodide has been achieved in eight steps and 20% overall yield from commercially available (S)-γ-hydroxymethyl-γ-butyrolactone.
Synthesis and antiviral evaluation of cyclic and acyclic 2-methyl-3-hydroxy-4-pyridinone nucleoside derivatives
Barral, Karine,Balzarini, Jan,Neyts, Johan,De Clercq, Erik,Hider, Robert C.,Camplo, Michel
, p. 43 - 50 (2007/10/03)
A series of cyclic and acyclic nucleoside analogues derived from 3-hydroxy-4-pyridinone were synthesized using the Vorbrüggen reaction. Iron chelation studies, and antiviral evaluation against a broad panel of viruses, were performed. The pKa value of ligand 25 and the stability constant of the corresponding iron-(III) complex were compared to those of deferiprone. The pFe3+ values were found to be similar. Some compounds showed moderate activity against both wild-type HSV-1 and HSV-2, as well as against a thymidine kinase deficient strain of HSV-1. These results suggest a novel mode of action for this group of nucleoside analogues.
Stereoselective C-glycosylation reactions of ribose derivatives: Electronic effects of five-membered ring oxocarbenium ions
Larsen, Catharine H.,Ridgway, Brian H.,Shaw, Jared T.,Smith, Deborah M.,Woerpel
, p. 10879 - 10884 (2007/10/03)
The factors controlling the highly α-selective C-glycosylation of ribose derivatives were determined by examining the Stereoselective reactions of 18 ribose analogues differing in substitution at C-2, C-3, and C-4. The lowest energy conformers of the intermediate oxocarbenium ions display the C-3 alkoxy group in a pseudoaxial orientation to maximize electrostatic effects. To a lesser extent, the C-2 substituent prefers a pseudoequatorial position, and the alkyl group at C-4 has little influence on conformational preferences. In all cases, the product was formed by stereoelectronically preferred inside attack on the lowest energy conformer.
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols
Buffet, Marianne F.,Dixon, Darren J.,Ley, Steven V.,Reynolds, Dominic J.,Storer, R. Ian
, p. 1145 - 1154 (2007/10/03)
Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads to the formation of the corresponding carbon linked alkynol products that can be further manipulated to produce key structural motifs and building blocks for the assembly of complex molecules.
Synthesis and antiviral evaluation of 3-hydroxy-2-methylpyridin-4-one dideoxynucleoside derivatives
Barral, Karine,Hider, Robert C.,Balzarini, Jan,Neyts, Johan,De Clercq, Erik,Camplo, Michel
, p. 4371 - 4374 (2007/10/03)
We describe the synthesis and the antiviral evaluation of novel α and β dideoxynucleoside derivatives in which the base has been replaced by a 3-hydroxy-2-methylpyridin-4-one. The syntheses were successfully achieved by the use of the standard Vorbrueggen coupling conditions. Moderate activity of these compounds were found on herpes simplex virus (HSV) type 1 and type 2.
The total synthesis of the annonaceous acetogenin, muricatetrocin C
Dixon, Darren J.,Ley, Steven V.,Reynolds, Dominic J.
, p. 1621 - 1636 (2007/10/03)
The total synthesis of the potential antitumour agent muricatetrocin C has provided an ideal stage for the exploitation and development of new chemistry. A convergent synthetic strategy has been realised incorporating three distinct pieces of methodology, these include a highly diastereoselective hetero-Diels -Alder reaction to construct the butenolide terminus, an oxygen to carbon rearrangement to install the trans-2,5-disubstituted tetrahydrofuran ring and a spatial desymmetrisation process to afford the anti-diol unit.
Synthetic approach to analogues of the original structure of sclerophytin A
Jung, Michael E.,Pontillo, Joseph
, p. 6848 - 6851 (2007/10/03)
A route to analogues of the original structure of sclerophytin A is described. The β-anomer of dideoxyribosyl nitriles 10a,b (prepared from glutamic acid) was converted into the methyl ketone 11. Addition of a silylated acetylide to 11 in diethyl ether/trimethylamine gave mainly 22a. Alkylation with methallyl halide and ozonolysis gave the ketone 24, which was then converted by hydrogenation and a second ozonolysis into the keto aldehyde 26. A two-step aldol process afforded the desired 3-pyrone 27 in good overall yield. However, several methods for the conversion of this enone 27 into the desired sclerophytin analogue 2 failed.
A short and efficient stereoselective synthesis of the potent 5-lipoxygenase inhibitor, CMI-977
Dixon,Ley,Reynolds,Chorghade
, p. 1043 - 1053 (2007/10/03)
A short and efficient synthesis of the potent 5-lipoxygenase inhibitor CMI-977 has been accomplished, utilising an oxygen to carbon rearrangement of an anomerically linked alkynyl stannane tetrahydrofuranyl ether derivative as the key step.
