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Medicinal-Pharmaceutical Chemistry Commons

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Full-Text Articles in Medicinal-Pharmaceutical Chemistry

Indole Anion Cycloadditions With Methyl Coumalate, George A. Kraus, Huangchao Yu Feb 2018

Indole Anion Cycloadditions With Methyl Coumalate, George A. Kraus, Huangchao Yu

Chemistry Publications

The reaction of the anion of indoles with methyl coumalate followed by selective opening of the lactone led to the preparation of tricyclic intermediates for indole alkaloid synthesis.


Synthesis, Self-Assembly, And Immunological Activity Of Α-Galactose-Functionalized Dendron–Lipid Amphiphiles, John Trant, Namrata Jain, D. M. Mazzuca, J Trevor Mcintosh, Bo Fan, S M Mansour Haeryfar, Sebastien Lecommandoux, Elizabeth Gillies Sep 2016

Synthesis, Self-Assembly, And Immunological Activity Of Α-Galactose-Functionalized Dendron–Lipid Amphiphiles, John Trant, Namrata Jain, D. M. Mazzuca, J Trevor Mcintosh, Bo Fan, S M Mansour Haeryfar, Sebastien Lecommandoux, Elizabeth Gillies

Chemistry Publications

Nanoassemblies presenting multivalent displays of biologically active carbohydrates are of significant interest for a wide array of biomedical applications ranging from drug delivery to immunotherapy. In this study, glycodendronlipid hybrids were developed as a new and tunable class of dendritic amphiphiles. A modular synthesis was used to prepare dendronlipid hybrids comprising distearylglycerol and 0 through 4th generation polyester dendrons with peripheral protected amines. Following deprotection of the amines, an isothiocyanate derivative of C-linked α-galactose (α-Gal) was conjugated to the dendron peripheries, affording amphiphiles with 1 to 16 α-Gal moieties. Self-assembly in water through a ...


Upgrading Malic Acid To Bio-Based Benzoates Via A Diels–Alder-Initiated Sequence With The Methyl Coumalate Platform, Jennifer J. Lee, Gerald R. Pollock Iii, Donald Mitchell, Lindsay Kasuga, George A. Kraus Sep 2014

Upgrading Malic Acid To Bio-Based Benzoates Via A Diels–Alder-Initiated Sequence With The Methyl Coumalate Platform, Jennifer J. Lee, Gerald R. Pollock Iii, Donald Mitchell, Lindsay Kasuga, George A. Kraus

Chemistry Publications

The conversion of naturally-occurring malic acid to the 2-pyrone methyl coumalate was optimized using a variety of acid catalysts. Coupling methyl coumalate with electron-rich dienophiles in an inverse electron-demand Diels–Alder (IEDDA)/decarboxylation/elimination domino sequence resulted in an investigation of the scope and limitations of the methodology. The thermal, metal-free, and one-pot procedure allows regioselective access to diverse aromatic compounds including tricyclic, biphenyl, and pyridinyl systems for elaboration. A comparison with analogous pyrones demonstrates the striking efficacy of methyl coumalate as a versatile platform for the generation of biorenewable functionalized benzoates.