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

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Editorial

Jump to: Research

Open AccessEditorial Melbourne-RACI December Synthesis Symposium
Molecules 2004, 9(6), 383-386; doi:10.3390/90600383
Received: 1 January 2004 / Published: 31 May 2004
PDF Full-text (125 KB) | HTML Full-text | XML Full-text
(This article belongs to the Special Issue RACI 2003 symposium)

Research

Jump to: Editorial

Open AccessArticle Self-associated, “Distillable” Ionic Media
Molecules 2004, 9(6), 387-393; doi:10.3390/90600387
Received: 18 February 2004 / Accepted: 22 February 2004 / Published: 31 May 2004
Cited by 49 | PDF Full-text (190 KB) | HTML Full-text | XML Full-text
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)
Open AccessArticle Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview
Molecules 2004, 9(6), 394-404; doi:10.3390/90600394
Received: 18 December 2003 / Accepted: 3 January 2004 / Published: 31 May 2004
Cited by 16 | PDF Full-text (205 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Synthesis of Chiral Building Blocks for Use in Drug Discovery
Molecules 2004, 9(6), 405-426; doi:10.3390/90600405
Received: 2 March 2004 / Accepted: 12 March 2004 / Published: 31 May 2004
Cited by 12 | PDF Full-text (290 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle The Preparation of Fluorescence-Quenched Probes for Use in the Characterization of Human Factor Xa Substrate Binding Domains
Molecules 2004, 9(6), 427-439; doi:10.3390/90600427
Received: 4 March 2004 / Accepted: 14 March 2004 / Published: 31 May 2004
Cited by 6 | PDF Full-text (212 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Nitrogen Heterocycles as Building Blocks for New Metallo-supramolecular Architectures
Molecules 2004, 9(6), 440-448; doi:10.3390/90600440
Received: 4 March 2004 / Accepted: 6 March 2004 / Published: 31 May 2004
Cited by 22 | PDF Full-text (195 KB) | HTML Full-text | XML Full-text
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)
Open AccessArticle Chiral Building Blocks: Enantioselective Syntheses of Benzyloxymethyl Phenyl Propionic Acids
Molecules 2004, 9(6), 449-458; doi:10.3390/90600449
Received: 14 May 2004 / Accepted: 27 May 2004 / Published: 31 May 2004
Cited by 3 | PDF Full-text (203 KB) | HTML Full-text | XML Full-text
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)
Open AccessArticle Development of Predictive Tools for Optimizing Organic Reactions
Molecules 2004, 9(6), 459-465; doi:10.3390/90600459
Received: 14 February 2004 / Accepted: 20 February 2004 / Published: 31 May 2004
Cited by 5 | PDF Full-text (150 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Preparation of Novel Selenopenams by Intramolecular Homolytic Substitution
Molecules 2004, 9(6), 466-471; doi:10.3390/90600466
Received: 17 February 2004 / Accepted: 20 February 2004 / Published: 31 May 2004
Cited by 13 | PDF Full-text (193 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Toward Pyridine-Fused Selenium-Containing Antioxidants
Molecules 2004, 9(6), 472-479; doi:10.3390/90600472
Received: 17 February 2004 / Accepted: 21 February 2004 / Published: 31 May 2004
Cited by 7 | PDF Full-text (228 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Self-Terminating, Oxidative Radical Cyclizations
Molecules 2004, 9(6), 480-497; doi:10.3390/90600480
Received: 23 February 2004 / Accepted: 1 March 2004 / Published: 31 May 2004
Cited by 13 | PDF Full-text (294 KB) | HTML Full-text | XML Full-text
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)
Open AccessArticle Synthesis of Pyran and Pyranone Natural Products
Molecules 2004, 9(6), 498-512; doi:10.3390/90600498
Received: 25 March 2004 / Accepted: 5 April 2004 / Published: 31 May 2004
Cited by 26 | PDF Full-text (247 KB) | HTML Full-text | XML Full-text
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
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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)
Open AccessArticle Synthesis and Characterisation of Macrocyclic Diamino Chiral Crown Ethers
Molecules 2004, 9(6), 513-519; doi:10.3390/90600513
Received: 4 March 2004 / Accepted: 10 March 2004 / Published: 31 May 2004
Cited by 19 | PDF Full-text (171 KB) | HTML Full-text | XML Full-text
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)

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