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Titolo:
VANADIUM(II)-INDUCED AND NIOBIUM(III)-INDUCED, DIASTEREOSELECTIVE PINACOL COUPLING OF PEPTIDE ALDEHYDES TO GIVE A C-2-SYMMETRICAL HIV PROTEASE INHIBITOR
Autore:
KAMMERMEIER B; BECK G; HOLLA W; JACOBI D; NAPIERSKI B; JENDRALLA H;
Indirizzi:
HOECHST AG,PHARMA FORSCH,POSTFACH 800320 D-65926 FRANKFURT GERMANY LANDES ENTWICKLUNGS GESELLSCH D-70182 STUTTGART GERMANY
Titolo Testata:
Chemistry
fascicolo: 3, volume: 2, anno: 1996,
pagine: 307 - 315
SICI:
0947-6539(1996)2:3<307:VANDP>2.0.ZU;2-D
Fonte:
ISI
Lingua:
ENG
Soggetto:
LOW-VALENT TITANIUM; ORGANIC-SYNTHESIS; STEREOCONTROLLED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CRYSTAL-STRUCTURE; AMINO-ACIDS; )V2CL3(THF)6>2)ZN2CL6>; NBCL3(DME); 1,2-DIOLS; SYMMETRY;
Keywords:
ENZYME INHIBITORS; NIOBIUM COMPLEXES; PEPTIDE ALDEHYDES; PINACOL COUPLING; VANADIUM COMPLEXES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
64
Recensione:
Indirizzi per estratti:
Citazione:
B. Kammermeier et al., "VANADIUM(II)-INDUCED AND NIOBIUM(III)-INDUCED, DIASTEREOSELECTIVE PINACOL COUPLING OF PEPTIDE ALDEHYDES TO GIVE A C-2-SYMMETRICAL HIV PROTEASE INHIBITOR", Chemistry, 2(3), 1996, pp. 307-315

Abstract

Peptide aldehydes 15 a-c are prepared without epimerization from enantiomerically pure (S)-alpha-amino acids (Scheme 3), Reductive pinacol homocoupling of 15 a-c, induced by vanadium complex 11 or niobium complex 16 in refluxing THF, yields C-2-symmetrical (S,R,R,S)-configurated6 a, 6 b and 2, respectively, with moderate to high stereoselectivity(Scheme 4), In a novel protocol for the preparation and utilization of THF solutions of 11, the isolation of air-sensitive intermediates can be avoided and the potent HIV protease inhibitor 2 prepared in enantio- and diastereomerically pure form on a kilogram scale without chromatographic purification. The (S,R,R,S) selectivity of the pinacol homocouplings is confirmed by means of an independent, stereochemically unequivocal synthesis of 6 a and 2 from D-mannitol 4 (Scheme 1).

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/04/20 alle ore 03:32:23