Next Issue
Volume 9, July
Previous Issue
Volume 9, May
 
 
molecules-logo

Journal Browser

Journal Browser

Molecules, Volume 9, Issue 6 (June 2004) – 13 articles , Pages 383-519

  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Reader to open them.
Order results
Result details
Section
Select all
Export citation of selected articles as:
171 KiB  
Article
Synthesis and Characterisation of Macrocyclic Diamino Chiral Crown Ethers
by Waldo H. Correa and Janet L. Scott
Molecules 2004, 9(6), 513-519; https://doi.org/10.3390/90600513 - 31 May 2004
Cited by 27 | Viewed by 8960
Abstract
A benign and efficient synthesis of chiral macrocyclic ‘aza-crown’ ethers of varying ring size is reported. The synthesis involves a Schiff base condensation of ether linked dialdehydes of varying chain length and (1R,2R)-(–)-1,2-diaminocyclohexane under mild conditions to yield the macrocycles, which are subsequently [...] Read more.
A benign and efficient synthesis of chiral macrocyclic ‘aza-crown’ ethers of varying ring size is reported. The synthesis involves a Schiff base condensation of ether linked dialdehydes of varying chain length and (1R,2R)-(–)-1,2-diaminocyclohexane under mild conditions to yield the macrocycles, which are subsequently reduced to yield the diamino analogues. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

247 KiB  
Article
Synthesis of Pyran and Pyranone Natural Products
by Christopher D. Donner, Melvyn Gill and Leonie M. Tewierik
Molecules 2004, 9(6), 498-512; https://doi.org/10.3390/90600498 - 31 May 2004
Cited by 43 | Viewed by 11568
Abstract
An overview of the synthesis of the fungal metabolites (+)-dermolactone, (–)- semixanthomegnin, (+)- and (–)-mellein, (–)-ochratoxin α, (–)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as [...] Read more.
An overview of the synthesis of the fungal metabolites (+)-dermolactone, (–)- semixanthomegnin, (+)- and (–)-mellein, (–)-ochratoxin α, (–)-(1R,3S)-thysanone, the enantiopure ventiloquinones L, E and G, and 8-desmethyleleutherin from a common chiral intermediate, is presented. Further methodology leading potentially toward extended quinones such as (3S,3'S)-xylindein is also outlined. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

294 KiB  
Article
Self-Terminating, Oxidative Radical Cyclizations
by Tim Dreessen, Christian Jargstorff, Lars Lietzau, Christian Plath, Arne Stademann and Uta Wille
Molecules 2004, 9(6), 480-497; https://doi.org/10.3390/90600480 - 31 May 2004
Cited by 16 | Viewed by 9907
Abstract
The recently discovered novel concept of self-terminating, oxidative radical cyclizations, through which alkynes can be converted into carbonyl compounds under very mild reaction conditions using O-centered inorganic and organic radicals as oxidants, is described Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

228 KiB  
Article
Toward Pyridine-Fused Selenium-Containing Antioxidants
by Tahli Fenner and Carl H. Schiesser
Molecules 2004, 9(6), 472-479; https://doi.org/10.3390/90600472 - 31 May 2004
Cited by 12 | Viewed by 7729
Abstract
Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2- (benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2- carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Work toward extending [...] Read more.
Photolysis of the thiohydroximate ester derivative 21 of 2-carboethoxy-2-(2- (benzylseleno)pyridin-3-yl)tridecylcarboxylic acid (20) affords 2-dodecyl-2- carboethoxy-2,3-dihydroselenolo[2,3-b]pyridine (22) in 89% yield in a process presumably involving intramolecular homolytic substitution by a tertiary alkyl radical at selenium with loss of a benzyl radical. Work toward extending this methodology to the preparation of pyridine-fused selenium analogues of antioxidants is described. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

193 KiB  
Article
Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution
by Michael W. Carland and Carl H. Schiesser
Molecules 2004, 9(6), 466-471; https://doi.org/10.3390/90600466 - 31 May 2004
Cited by 21 | Viewed by 6955
Abstract
Photolyses of the thiohydroximate ester derivatives 13 and 21 of the 4- (benzyl-seleno)-2-azetidinoines 7 and 20, afford the 1-aza-7-oxo-4-selenabicyclo- [3.2.0]heptane ring systems 14 and 21 in good to moderate yield in processes that presumably involve intramolecular homolytic substitution at selenium with expulsion of [...] Read more.
Photolyses of the thiohydroximate ester derivatives 13 and 21 of the 4- (benzyl-seleno)-2-azetidinoines 7 and 20, afford the 1-aza-7-oxo-4-selenabicyclo- [3.2.0]heptane ring systems 14 and 21 in good to moderate yield in processes that presumably involve intramolecular homolytic substitution at selenium with expulsion of benzyl radical. Extension of this methodology to the preparation of derivatives 24 of 12,2a-dihydro-1H,8H-azeto[2,1-b][1,3]benzoselenazin-1-one (22) is also described. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

150 KiB  
Article
Development of Predictive Tools for Optimizing Organic Reactions
by Brett A. Roberts and Christopher R. Strauss
Molecules 2004, 9(6), 459-465; https://doi.org/10.3390/90600459 - 31 May 2004
Cited by 6 | Viewed by 9030
Abstract
Although microwave chemistry and its applications have undergone rapid growth over the last decade, the technology is not yet employed routinely in all synthetic laboratories. A significant obstacle to implementation concerns the empirical work required to adapt established conditions into alternatives employing higher [...] Read more.
Although microwave chemistry and its applications have undergone rapid growth over the last decade, the technology is not yet employed routinely in all synthetic laboratories. A significant obstacle to implementation concerns the empirical work required to adapt established conditions into alternatives employing higher temperatures. We now have established predictive tools to translate reaction conditions from conventional heated (ambient pressure) to elevated temperature (ambient or elevated pressure). We have studied 45 reactions (including published literature examples) and made in excess of 200 estimations for specific yield or conversion, with a high degree of accuracy. Linear regression analysis of estimated vs. experimental conversion or yield was 0.90 (first iteration) and 0.98 (second iteration). Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

203 KiB  
Article
Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids
by Jack G. Parsons, Danuta Stachurska-Buczek, Neil Choi, Peter G. Griffiths, Daniel A. Huggins, Beata M. Krywult, Sharon T. Marino, Thao Nguyen, Craig S. Sheehan, Ian W. James, Andrew M. Bray, Jonathan M. White and Rustum S. Boyce
Molecules 2004, 9(6), 449-458; https://doi.org/10.3390/90600449 - 31 May 2004
Cited by 5 | Viewed by 10012
Abstract
The synthesis of (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)- propionic acid, (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methylphenyl)propionic acid and (2S)-2-benzyl-oxymethyl-3-(2,4-dimethylphenyl)propionic acid has been achieved by TiCl4 mediated alkylation of the corresponding (4R)-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl-, 2-fluoro-4-methylphenyl-, 2,4- dimethylphenyl-)propionyl]-2-oxazolidinones, followed by hydrolysis of the chiral auxiliary. The stereochemistry of the alkylation reaction was confirmed by an X-ray [...] Read more.
The synthesis of (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methoxyphenyl)- propionic acid, (2S)-2-benzyloxymethyl-3-(2-fluoro-4-methylphenyl)propionic acid and (2S)-2-benzyl-oxymethyl-3-(2,4-dimethylphenyl)propionic acid has been achieved by TiCl4 mediated alkylation of the corresponding (4R)-4-benzyl-3-[3-(2-fluoro-4-methoxyphenyl-, 2-fluoro-4-methylphenyl-, 2,4- dimethylphenyl-)propionyl]-2-oxazolidinones, followed by hydrolysis of the chiral auxiliary. The stereochemistry of the alkylation reaction was confirmed by an X-ray crystal structure of (4R)-4-benzyl-3-[(2S)-2-benzyloxymethyl-3-(2- fluoro-4-methylphenyl)propionyl]-2-oxazolidinone. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

195 KiB  
Article
Nitrogen Heterocycles as Building Blocks for New Metallo-supramolecular Architectures
by Peter J. Steel
Molecules 2004, 9(6), 440-448; https://doi.org/10.3390/90600440 - 31 May 2004
Cited by 26 | Viewed by 8085
Abstract
The syntheses of representative examples of five classes of new heterocyclic ligands are described. These include N,N'-chelating bis-heterocycles, binucleating ligands, cyclometallated compounds, chiral ligands and a family of polyheteroaryl-linked arenes. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

212 KiB  
Article
The Preparation of Fluorescence-Quenched Probes for Use in the Characterization of Human Factor Xa Substrate Binding Domains
by Karen M. Bromfield, Julia Cianci and Peter J. Duggan
Molecules 2004, 9(6), 427-439; https://doi.org/10.3390/90600427 - 31 May 2004
Cited by 8 | Viewed by 9575
Abstract
The preparation and characterization by LCMS of a library of 55 fluorescence- quenched peptides is described. The peptides bear a terminal anthranilamide fluorophore and a penultimate 2,4-dinitrophenyl-L-lysine quencher, and will be used to probe the substrate binding domain of the human blood coagulation [...] Read more.
The preparation and characterization by LCMS of a library of 55 fluorescence- quenched peptides is described. The peptides bear a terminal anthranilamide fluorophore and a penultimate 2,4-dinitrophenyl-L-lysine quencher, and will be used to probe the substrate binding domain of the human blood coagulation enzyme, factor Xa. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

290 KiB  
Article
Synthesis of Chiral Building Blocks for Use in Drug Discovery
by Sharon T. Marino, Danuta Stachurska-Buczek, Daniel A. Huggins, Beata M. Krywult, Craig S. Sheehan, Thao Nguyen, Neil Choi, Jack G. Parsons, Peter G. Griffiths, Ian W. James, Andrew M. Bray, Jonathan M. White and Rustum S. Boyce
Molecules 2004, 9(6), 405-426; https://doi.org/10.3390/90600405 - 31 May 2004
Cited by 25 | Viewed by 16016
Abstract
In the past decade there has been a significant growth in the sales of pharmaceutical drugs worldwide, but more importantly there has been a dramatic growth in the sales of single enantiomer drugs. The pharmaceutical industry has a rising demand for chiral intermediates [...] Read more.
In the past decade there has been a significant growth in the sales of pharmaceutical drugs worldwide, but more importantly there has been a dramatic growth in the sales of single enantiomer drugs. The pharmaceutical industry has a rising demand for chiral intermediates and research reagents because of the continuing imperative to improve drug efficacy. This in turn impacts on researchers involved in preclinical discovery work. Besides traditional chiral pool and resolution of racemates as sources of chiral building blocks, many new synthetic methods including a great variety of catalytic reactions have been developed which facilitate the production of complex chiral drug candidates for clinical trials. The most ambitious technique is to synthesise homochiral compounds from non-chiral starting materials using chiral metal catalysts and related chemistry. Examples of the synthesis of chiral building blocks from achiral materials utilizing asymmetric hydrogenation and asymmetric epoxidation are presented. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

205 KiB  
Article
Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview
by Margaret A. Brimble
Molecules 2004, 9(6), 394-404; https://doi.org/10.3390/90600394 - 31 May 2004
Cited by 20 | Viewed by 9042
Abstract
The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal [...] Read more.
The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal containing natural products such as the polyether antibiotics salinomycin and CP44,161 and the shellfish toxins, the spirolides. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

190 KiB  
Article
Self-associated, “Distillable” Ionic Media
by Ulf P. Kreher, Anthony E. Rosamilia, Colin L. Raston, Janet L. Scott and Christopher R. Strauss
Molecules 2004, 9(6), 387-393; https://doi.org/10.3390/90600387 - 31 May 2004
Cited by 71 | Viewed by 10720
Abstract
Liquid or low melting association products of carbon dioxide and a secondary amine, both neutral molecules that may be gaseous, are recognised as “distillable” ionic media. Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Show Figures

Figure 1

125 KiB  
Editorial
Melbourne-RACI December Synthesis Symposium
by Melvyn Gill
Molecules 2004, 9(6), 383-386; https://doi.org/10.3390/90600383 - 31 May 2004
Cited by 7 | Viewed by 4521
Abstract
This special issue of Molecules celebrates the Synthesis Symposium held in The School of Chemistry at the University of Melbourne during the first week of December each and every year since 1976.[...] Full article
(This article belongs to the Special Issue RACI 2003 symposium)
Previous Issue
Next Issue
Back to TopTop