Journal ArticleDOI
A straightforward synthesis of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid)
TLDR
Based on the oxidation of corresponding terminal alkynes to α-keto esters, DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) in its pyranose-furanose mixture form was efficiently synthesized as discussed by the authors.Abstract:
Based on the oxidation of corresponding terminal alkynes to α-keto esters, DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) in its pyranose form and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) in its protected pyranose–furanose mixture form were efficiently synthesized. These terminal alkynes were in turn obtained by C1- or C3-homologation of corresponding protected sugars, respectively. Along with the application of this strategy, the syntheses of two C6-ulosonic acids, 3-deoxy-D-erythro-hex-2-ulosonic acid and 3-deoxy-L-erythro-hex-2-ulosonic acid in their protected pyranose form, were also described.read more
Citations
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Journal ArticleDOI
1,3-Phenylene bis(ketoacid) derivatives as inhibitors of Escherichia coli dihydrodipicolinate synthase.
TL;DR: A series of phenolic ketoacid derivatives that mimic the proposed enzymatic intermediate were designed as potential inhibitors of this enzyme and were synthesized from simple precursors and shown to act as slow and slow-tight binding inhibitors.
Journal ArticleDOI
Synthesis of 4-azido-4-deoxy-Neu5,7,8,9Ac(4)2en1Me. A key intermediate for the synthesis of GG167 from D-glucono-delta-lactone
TL;DR: Stereoselective synthesis of 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D -galacto-non-2-enonic acid methyl ester, an advanced key intermediate for the synthesis of neuraminidase inhibitor GG167 (Zanamivir, Relenza), was accomplished
Journal ArticleDOI
Synthesis of a new stable conformationally constrained 2,7-anhydrosialic acid derivative.
TL;DR: A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from d-glucono-delta-lactone using a highly syn-selective addition of Grignard reagent to the N-benzylimine 8.
Journal ArticleDOI
Total Synthesis of Spiromamakone A and Structure Revision of Spiropreussione A.
TL;DR: The synthesis using optically active intermediates enabled identification of the racemization step of spiromamakone A and revealed that spiropreussione A are identical; the latter had been reported as a constitutional isomer of the other.
References
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Book ChapterDOI
The Chemistry and Biological Significance of 3-Deoxy-d-manno-2-Octulosonic Acid (KDO)*
TL;DR: It is found that when oligosaccharides containing reducing-terminal KDO residues are subjected to borohydride reduction prior to Smith degradation, the epimeric pair of oligosACcharides is obtained, containing 3-deoxy- L - ribo - and - arabino -hexonic acid at the end that had formerly been reducing.
Journal ArticleDOI
From glucose to aromatics: recent developments in natural products of the shikimic acid pathway
Journal ArticleDOI
Installation of the Pyruvate Unit in Glycidic Aldehydes via a Wittig Olefination-Michael Addition Sequence Utilizing a Thiazole-Armed Carbonyl Ylide. A New Stereoselective Route to 3-Deoxy-2-Ulosonic Acids and the Total Synthesis of DAH, KDN, and 4-epi-KDN
Journal ArticleDOI
Formal Synthesis of 3-Deoxy-d-manno-2-Octulosonic Acid (KDO) via a Highly Double-Stereoselective Hetero Diels−Alder Reaction Directed by a (Salen)CoII Catalyst and Chiral Diene
TL;DR: This paper presents a formal total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) based on a highly double-stereoselective hetero Diels-Alder reaction between an electron-rich diene and ethyl glyoxylate catalyzed by (Salen)Co(II) complex, a new catalyst for Diels -Alder reactions.
Journal ArticleDOI
Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates.
TL;DR: The total synthesis of two mono-THF acetogenins, tonkinecin and annonacin, is reported in full detail.
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