Enantioselective Total Synthesis of (1R,3S,4R,5R)-1-Amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic Acid. A Full-Aldol Access to Carbaketose Derivatives (Articolo in rivista)

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  • Enantioselective Total Synthesis of (1R,3S,4R,5R)-1-Amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic Acid. A Full-Aldol Access to Carbaketose Derivatives (Articolo in rivista) (literal)
Anno
  • 2004-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/jo035846a (literal)
Alternative label
  • Battistini L.; Curti C.; Zanardi F.; Rassu G.; Auzzas L.; Casiraghi G (2004)
    Enantioselective Total Synthesis of (1R,3S,4R,5R)-1-Amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic Acid. A Full-Aldol Access to Carbaketose Derivatives
    in Journal of organic chemistry; ACS, American chemical society, Washington, DC (Stati Uniti d'America)
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Battistini L.; Curti C.; Zanardi F.; Rassu G.; Auzzas L.; Casiraghi G (literal)
Pagina inizio
  • 2611 (literal)
Pagina fine
  • 2613 (literal)
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  • http://pubs.acs.org/doi/pdf/10.1021/jo035846a (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 69 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 3 (literal)
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  • 7 (literal)
Note
  • Scopu (literal)
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Dipartimento Farmaceutico, Universita` di Parma, Parco Area delle Scienze 27A, I-43100 Parma, Italy, and Istituto di Chimica Biomolecolare del CNR, Sezione di Sassari, Traversa La Crucca 3, I-07040 Li Punti, Sassari, Italy (literal)
Titolo
  • Enantioselective Total Synthesis of (1R,3S,4R,5R)-1-Amino-4,5-dihydroxycyclopentane-1,3-dicarboxylic Acid. A Full-Aldol Access to Carbaketose Derivatives (literal)
Abstract
  • The enantioselective synthesis of cyclopentanedicarboxylic amino acid 1, a novel rigid and functionalized L-glutamic acid analogue, has been achieved in 15 linear steps from silyloxypyrrole 3, utilizing L-glyceraldehyde 4 as the source of chirality. The key steps in the synthesis are three sequential aldol-based carbon-carbon bond-forming reactions: two crossed vinylogous aldol additions (2 + 3 f 8 and 4 + 5 f 10 + 11) and one intramolecular silylative aldolization (6 f 7). En passant, the short syntheses of (2S)- 2-hydroxymethylglutamic acid (16) and its (2R)-enantiomer ent-16, a potent metabotropic glutamate receptor agonist, have been achieved. (literal)
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