An Efficient Approach to the Synthesis of Ethyl Esters of 2,6-Anhydro-3-Deoxy-D-GlucoAnd D-Allo-Heptanoates
- 1 January 1999
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 18 (9) , 1067-1077
- https://doi.org/10.1080/07328309908544055
Abstract
An efficient synthesis of analogues of DAH (3-deoxy-D-arabino-hept-2-ulosonic acid) and DRH (3-deoxy-D-ribo-hept-2-ulosonic acid) is described. The route exploits a previously published highly double-stereoselective hetero Diels-Alder reaction catalyzed by a chiral salenCo(II) complex. Asymmetric dihydroxylation followed by selective reduction leads to stereoselective introduction of hydroxy groups at C-4 and C-5. Oxidative cleavage of the C-6 side-chain, in situ reduction of the resulting aldehyde and deprotection afford the desired targets, which may be useful precursors to the simple analogues of the anti-influenza agent GG167.Keywords
This publication has 10 references indexed in Scilit:
- An Efficient Approach to the 2-Nonulosonic Acid Skeleton Through a Hetero-Diels-Alder ReactionJournal of Carbohydrate Chemistry, 1998
- Asymmetric hetero-Diels–Alder reaction of 1-alkyl-3-silyloxy-1,3-dienes with ethyl glyoxylate catalyzed by a chiral (salen)cobalt(II) complexTetrahedron: Asymmetry, 1998
- 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 DieneThe Journal of Organic Chemistry, 1998
- A Concise Synthesis of (±) Ketodeoxyheptulosonic Acid Derivatives Via Aqueous Hetero Diels Alder Reaction and NBS Mediated DibrominationJournal of Carbohydrate Chemistry, 1995
- Synthesis of 6-, 7- and 8-carbon sugar analogues of potent anti-influenza 2,3-didehydro-2,3-dideoxy-N-acetylneuraminic acid derivativesJournal of the Chemical Society, Perkin Transactions 1, 1995
- 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-KDNJournal of the American Chemical Society, 1994
- Published by American Chemical Society (ACS) ,1993
- Chemoselective hydrolysis of terminal isopropylidene acetals and subsequent glycol cleavage by periodic acid in one potThe Journal of Organic Chemistry, 1993
- .alpha.-Hydroxy ketones in high enantiomeric purity from asymmetric dihydroxylation of enol ethersThe Journal of Organic Chemistry, 1992
- Chemistry of the enolates of 2-acetylthiazole: aldol reactions with chiral aldehydes to give 3-deoxy aldos-2-uloses and 3-deoxy 2-ulosonic acids. A short total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO)The Journal of Organic Chemistry, 1991