http://www.cnr.it/ontology/cnr/individuo/prodotto/ID15104
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)
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- http://pubs.acs.org/doi/pdf/10.1021/jo035846a (literal)
- Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
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- 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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