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1.
ACS Omega ; 2(2): 698-711, 2017 Feb 28.
Article in English | MEDLINE | ID: mdl-31457465

ABSTRACT

Long-range olefin isomerization of 2-alkenylbenzoic acid derivatives going through two to five sp3-carbon atoms to give (E)-alkenes was achieved with palladium(0) nanoparticles. The substrate scope of this reaction includes carboxylic acid, ester, and primary to tertiary amides and tolerates various substituents on the benzene ring. This isomerization reaction was catalyzed by recyclable Pd(0) nanoparticles, prepared in situ from PdCl2 and characterized by X-ray powder diffraction and scanning electron microscopy analyses. 1H NMR studies and kinetic modeling supported a stepwise process. This new process was applied to synthesize a natural dihydroisocoumarin with good efficiency.

2.
Org Lett ; 18(4): 808-11, 2016 Feb 19.
Article in English | MEDLINE | ID: mdl-26844691

ABSTRACT

A new immunostimulant, the 4'-epimer of α-C-GalCer, was synthesized from a C2-symmetric dienediol and α-C-allyl galactoside. The intramolecular aziridination and the following reductive ring opening provided the core of the aliphatic amino alcohol with excellent regio- and stereocontrol. The new immunostimulants 3d and 3e gave a better polarized Th1-type cytokine response in murine NKT cells than the benchmarked α-C-GalCer.


Subject(s)
Adjuvants, Immunologic/chemical synthesis , Aziridines/chemistry , Galactosylceramides/chemical synthesis , Galactosylceramides/pharmacology , Adjuvants, Immunologic/chemistry , Adjuvants, Immunologic/pharmacology , Animals , Cardiac Glycosides , Cytokines , Galactosylceramides/chemistry , Glycosides , Marine Biology , Mice , Mice, Inbred BALB C , Molecular Structure , Monosaccharides/chemistry , Natural Killer T-Cells , Porifera/chemistry , Stereoisomerism
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