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Titolo:
PRACTICAL ASYMMETRIC-SYNTHESIS OF EFAVIRENZ (DMP-266), AN HIV-1 REVERSE-TRANSCRIPTASE INHIBITOR
Autore:
PIERCE ME; PARSONS RL; RADESCA LA; LO YS; SILVERMAN S; MOORE JR; ISLAM Q; CHOUDHURY A; FORTUNAK JMD; NGUYEN D; LUO C; MORGAN SJ; DAVIS WP; CONFALONE PN; CHEN CY; TILLYER RD; FREY L; TAN LS; XU F; ZHAO DL; THOMPSON AS; CORLEY EG; GRABOWSKI EJJ; REAMER R; REIDER PJ;
Indirizzi:
DUPONT MERCK PHARMACEUT CO,CHEM PROC R&D DEPT,PROC RES FACIL DEEP WATER NJ 08023 MERCK & CO INC,MERCK SHARP & DOHME RES LABS,DEPT PROC RES RAHWAY NJ 07065
Titolo Testata:
Journal of organic chemistry
fascicolo: 23, volume: 63, anno: 1998,
pagine: 8536 - 8543
SICI:
0022-3263(1998)63:23<8536:PAOE(A>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE ADDITION; ALDEHYDES; ACETYLIDE; L-743,726; DMP-266;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
28
Recensione:
Indirizzi per estratti:
Citazione:
M.E. Pierce et al., "PRACTICAL ASYMMETRIC-SYNTHESIS OF EFAVIRENZ (DMP-266), AN HIV-1 REVERSE-TRANSCRIPTASE INHIBITOR", Journal of organic chemistry, 63(23), 1998, pp. 8536-8543

Abstract

A highly enantioselective and practical synthesis of the HIV-1 reverse transcriptase inhibitor efavirenz (1) is described. The synthesis proceeds in 62% overall yield in seven steps from 4-chloroaniline (6) togive efavirenz (1) in excellent chemical and optical purity. A novel,enantioselective addition of Li-cyclopropyl acetylide (4a) top-methoxybenzyl-protected ketoaniline 3a mediated by (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide (5a) establishes the stereogenic center in the target with a remarkable level of stereocontrol.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 05/12/20 alle ore 14:01:22