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Titolo:
Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine
Autore:
Adamczyk, M; Akireddy, SR; Reddy, RE;
Indirizzi:
Abbott Labs, Div Diagnost, Dept Chem 9 NM, Abbott Pk, IL 60064 USA Abbott Labs Abbott Pk IL USA 60064 ept Chem 9 NM, Abbott Pk, IL 60064 USA
Titolo Testata:
ORGANIC LETTERS
fascicolo: 20, volume: 3, anno: 2001,
pagine: 3157 - 3159
SICI:
1523-7060(20011004)3:20<3157:ESO(VC>2.0.ZU;2-K
Fonte:
ISI
Lingua:
ENG
Soggetto:
ANTIBIOTIC L-AZATYROSINE; AMINO-ACID-ANALOGS; ASYMMETRIC HYDROGENATION; CONCISE SYNTHESIS; RAS; CELLS; EFFICIENT; PROTEIN; OOCYTES; PEPTIDE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
43
Recensione:
Indirizzi per estratti:
Indirizzo: Adamczyk, M Abbott Labs, Div Diagnost, Dept Chem 9 NM, Bldg AP20,100 Abbott Pk Rd, Abbott Pk, IL 60064 USA Abbott Labs Bldg AP20,100 Abbott Pk Rd Abbott Pk IL USA 60064
Citazione:
M. Adamczyk et al., "Enantioselective synthesis of (2-pyridyl)alanines via catalytic hydrogenation and application to the synthesis of L-azatyrosine", ORG LETT, 3(20), 2001, pp. 3157-3159

Abstract

GRAPHICSA novel method for the synthesis of (2-pyridyl)alanines 2a-b was developedby converting (2-pyridyl)dehydroamino acid derivatives 1a-b to the corresponding N-oxides 3a-b followed by asymmetric hydrogenation using (RR)-[Rh(Et-DUPHOS)(COD)]BF4 [(RR)-6] catalyst and subsequent N-oxide reduction in 80-83% ee. This methodology was applied to the total synthesis of L-azatyrosine [(+)-12], an antitumor antibiotic, starting from (5-benzyloxy)-2-pyridylmethanol (7), in > 96% enantiomeric purity.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 27/09/20 alle ore 06:36:28