Synthetic applications of the baylis-hillman reaction: simple synthesis of [2E]-2-butyloct-2-enal and [2E]-2-tridecylheptadec-2-enal

A simple synthesis of [2E]-2-butyloct-2-enal, an alarm pheromone component of the African weaver ant, Oeco-phylla longinoda, and [2E]-2-tridecylheptadec-2-enal, an unusual metabolite from the red alga, Laurencia species using Baylis-Hillman adducts has been described

The Baylis-Hillman reaction: a novel carbon-carbon bond forming reaction

This article does not have an abstract

The friedel-crafts reaction of the Baylis-Hillman adducts

A simple and convenient methodology for the stereoselective construction of 2-benzyl substituted trisubstituted olefins via sulfuric acid catalyzed Fredel-Crafts reaction of benzene with Baylis-Hillman adducts is described

The Baylis-Hillman reaction: an expedient synthesis of (Z)-keto allyl bromides and chlorides

A simple and expedient synthesis of (Z)-keto allyl bromides and chlorides, from the Baylis-Hillman adducts is described

Stereoselective transformation of Baylis-Hillman adducts into (3E)-3-(alkoxymethyl)alk-3-en-2-ones

The pure (3E)-3-(methoxymethyl)alk-3-en-2-ones and (3E)-3-(ethoxymethyl)alk-3-en-2-ones are formed in the acid induced reaction of 4-hydroxy-3-methylenealkan-2-ones with methanol and ethanol, respectively

A facile one-pot conversion of acetates of the Baylis-Hillman adducts to [E]-α-methylcinnamic acids

A simple and convenient stereoselective synthesis of [E]-α-methylcinnamic acids via the nucleophilic addition of hydride ion from sodium borohydride to methyl 3-acetoxy-3-aryl-2-methylenepropanoates followed by hydrolysis and crystallization is described. Efficacy of this methodology in the synthesis of [E]-p-(myristyloxy)-α-methylcinnamic acid, an active hypolipidemic agent, and [E]-p-(carbomethoxy)-α -methylcinnamic acid, a valuable synthon for an orally active serine protease inhibitor, is also demonstrated

Structured materials syntheses in a self-assembled surfactant mesophase

A self-assembled surfactant mesophase containing AOT/lecithin/isooctane/water has been exploited as a template for the syntheses of nanostructured materials. The system is a gel sustaining equal volumes of an aqueous phase and an organic hydrocarbon phase. We have explored the synthesis of extended ceramic and polymer structures in this gel phase. Iron nanoparticles synthesized in the microaqueous phase have chain-like structures, while porous silica structures are obtained using precursors soluble in the organic microphase. The retention of catalytic activity of an oxidative enzyme in the microaqueous phase allows synthesis of structured polymers at the oil-water interface. (C) 2000 Elsevier Science B.V

Ribonucleoside Analogue That Blocks Replication of Bovine Viral Diarrhea and Hepatitis C Viruses in Culture

A base-modified nucleoside analogue, β-d-N(4)-hydroxycytidine (NHC), was found to have antipestivirus and antihepacivirus activities. This compound inhibited the production of cytopathic bovine viral diarrhea virus (BVDV) RNA in a dose-dependant manner with a 90% effective concentration (EC(90)) of 5.4 μM, an observation that was confirmed by virus yield assays (EC(90) = 2 μM). When tested for hepatitis C virus (HCV) replicon RNA reduction in Huh7 cells, NHC had an EC(90) of 5 μM on day 4. The HCV RNA reduction was incubation time and nucleoside concentration dependent. The in vitro antiviral effect of NHC was additive with recombinant alpha interferon-2a and could be prevented by the addition of exogenous cytidine and uridine but not of other natural ribo- or 2′-deoxynucleosides. When HCV RNA replicon cells were cultured in the presence of increasing concentrations of NHC (up to 40 μM) for up to 45 cell passages, no resistant replicon was selected. Similarly, resistant BVDV could not be selected after 20 passages. NHC was phosphorylated to the triphosphate form in Huh7 cells, but in cell-free HCV NS5B assays, synthetic NHC-triphosphate (NHC-TP) did not inhibit the polymerization reaction. Instead, NHC-TP appeared to serve as a weak alternative substrate for the viral polymerase, thereby changing the mobility of the product in polyacrylamide electrophoresis gels. We speculate that incorporated nucleoside analogues with the capacity of changing the thermodynamics of regulatory secondary structures (with or without introducing mutations) may represent an important class of new antiviral agents for the treatment of RNA virus infections, especially HCV