Modification of C-terminal peptides to form peptide enamides: synthesis of chondriamides A and C.
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Alkenes↗
Biomedical subjects
J A Porco
Publications and source records attributed to J A Porco.
Total synthesis of the NF-kappa B inhibitor (-)-cycloepoxydon: utilization of tartrate-mediated nucleophilic epoxidation.
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Epoxy Compounds↗
Exploring chemical diversity of epoxyquinoid natural products: synthesis and biological activity of (-)-jesterone and related molecules.
Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epoxide intermediate.
Alkenes↗
Parallel synthesis and purification using anthracene-tagged substrates.
[reaction: see text] A new strategy for the synthesis and purification of synthetic intermediates is described using anthracene-tagged ester substrates in conjunction with an N-benzylmaleimide resin. Anthracene chemical tags permit use of standard solution-phase reaction conditions and reaction-monitoring techniques.
Anthracenes↗
Polymer supports for streamlined organic synthesis.
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Chemistry, Organic↗
Streamlined synthesis of substituted 2-aminothiazoles using tandem precipitative and polymer-assisted reactions.
The tactical combination of classical product precipitation and subsequent modification of precipitated products using polymer-assisted transformations has been employed in the preparation of substituted 2-aminothiazole derivatives. 2-aminothiazoles were precipitated in parallel as hydrobromide monohydrate salts, directly redissolved, and reacted further using polymer-supported reagents to afford free-based 2-aminothiazoles, aminothiazoyloxamates, and aminothiazoylamides.
Antiviral Agents↗
Organic synthesis using chemical tags: the third Leg of parallel synthesis.
Increasing emphasis has recently been placed on the development of synthetic methods which effectively couple chemical synthesis and purification. For example, new formats for parallel synthesis are being developed which involve attachment of chemical tags to both reagents, reactants, and substrates to permit their chemoselective removal from reaction mixtures. The driving force for the development of tagged organic reagents is the ability to use standard solution-phase chemistry methods and reaction monitoring techniques (e.g. TLC and HPLC). In this mini-review, we will outline recent developments on the growing class of chemically tagged reagents, reactants, and substrates and highlight examples of their use in multistep synthesis.
Chromatography, Affinity↗
Parallel synthesis of 1,2,4-oxadiazoles using CDI activation.
1,2,4-Oxadiazoles have been prepared in parallel using 1,1'-carbonyldiimidazole (CDI) as a reagent for both formation and cyclodehydration of O-acyl benzamidoximes. The use of CDI facilitates parallel purification of the oxadiazole products by simple liquid-liquid extraction and filtration.
Benzamidines↗
Automated chemical synthesis: from resins to instruments.
Solid-phase organic synthesis is now a prevalent activity in drug discovery. In keeping with this keen interest is the need to develop reliable automated synthesis instrumentation as well as polymeric supports and linkers suitable for the full range of organic synthesis applications. In this paper, we review our activities in the development of new and enabling tools for automated chemical synthesis, including the following: (i) new solid supports such as ArgoGel (PS-PEG-based) and Argo-X203 (PS-based); and (ii) the Nautilus 2400 system, a fully closed and inert automated chemistry development workstation. Selected chemistry optimization and synthesis examples performed on the Nautilus and new solid supports will be described.
Automation↗