A concise, stereocontrolled synthesis of (+)-polyoxamic acid was achieved. Starting from trans-oxazoline as a chiral building block, the key step involves diastereoselective oxazine formation catalyzed by palladium(0).
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Synthesis of polyurethanes through the oxidative decarboxylation of oxamic acids: a new gateway toward self-blown foams.
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University of Bordeaux, CNRS, Bordeaux INP, LCPO, UMR 5629 16 Avenue Pey-Berland F-33600 Pessac France
Polyurethane (PU) thermoplastics and thermosets were prepared through the step-growth polymerization of generated polyisocyanates through the decarboxylation of polyoxamic acids, in the presence of phenyliodine diacetate (PIDA), and polyols. The CO produced during the reaction allowed the access to self-blown polyurethane foams through an endogenous chemical blowing. The acetic acid released from ligand exchange at the iodine center was also shown to accelerate the polymerization reaction, avoiding the recourse to an additional catalyst.
View Article and Find Full Text PDFTotal Synthesis of (+)-Polyoxamic Acid via Visible-Light-Mediated Photocatalytic β-Scission and 1,5-Hydrogen Atom Transfer of Glucose Derivative.
J Org Chem
June 2020
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan.
A total synthesis of polyoxamic acid has been achieved. The key feature of the synthetic route is a visible-light-mediated β-scission and carbon-to-carbon 1,5-hydrogen atom transfer (1,5-HAT) to provide the functionalized alditol under mild conditions. This type of carbon-to-carbon 1,5-HAT initiated by C(sp)-centered radicals has been scarcely reported.
View Article and Find Full Text PDF[Stereoselective synthesis of polyhydroxylated amines using (S)-pyroglutamic acid derivatives].
Yakugaku Zasshi
August 2014
School of Pharmacy, Shujitsu University.
Naturally occurring polyhydroxylated amines such as (+)-1-deoxynojirimycin, polyoxamic acid, anisomycin, (-)swainsonine, and alexine stereoisomers, which have interesting biological activities including glucosidase- and mannosidase-inhibitory activity, immunoregulatory activity, and antibacterial effects, were synthesized stereoselectively starting from (S)-pyroglutamic acid derivatives. α,β-Unsaturated lactams ((S)-5-hydroxymethyl-2-oxo-3-pyrroline derivatives), α,β-unsaturated δ-lactone ((S)-4-amino-2-penten-5-olide derivative), and E-olefin ((S,E)-methyl-4-amino-5-hydroxypent-2-enoate derivative) from (S)-pyroglutamic acid derivatives were dihydroxylated using OsO4 in the presence of N-methyl morpholine N-oxide (NMO) to afford various chiral building blocks with different configurations. The stereoselectivity of cis-dihydroxylation for α,β-unsaturated lactams and α,β-unsaturated δ-lactone was very high, while the stereoselectivity was low for E-olefin.
View Article and Find Full Text PDFAn enantioselective synthesis of (+)-polyoxamic acid via phase-transfer catalytic conjugate addition and asymmetric dihydroxylation.
J Org Chem
January 2011
Marine Natural Products Chemistry Laboratory, Korea Ocean Research and Development Institute, Ansan 426-744, Korea.
A new enantioselective synthetic method of (+)-polyoxamic acid is reported. (+)-Polyoxamic acid could be obtained in 7 steps with 46% overall yield from diphenylmethyl-glycineimine tert-butyl ester via an enantioselective phase-transfer conjugate addition (99% yield, 96% ee) and an asymmetric dihydroxylation (98% yield, 94% de) as the key reactions.
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Acc Chem Res
October 2010
State Key Laboratory of Applied Organic Chemistry, and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
Amino acids are one of the most important classes of the building blocks of life: they are the structural subunits of proteins, peptides, and many secondary metabolites. In addition to the 20 α-amino acids that constitute the backbone of proteins, hundreds of other natural α-amino acids have been discovered either in free form or as components in natural products. The difference between these molecules is the substituents at the chiral carbon situated between the amino and carboxyl moieties; this carbon (and any atom along a chain attached to it) is thus an important synthetic target.
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