Concise and stereocontrolled synthesis of pseudo-C2-symmetric diamino alcohols and triamines for use in HIV protease inhibitors.
J Org Chem
; 68(4): 1418-25, 2003 Feb 21.
Article
en En
| MEDLINE
| ID: mdl-12585882
ABSTRACT
A new protocol is described for the stereocontrolled synthesis of pseudo-C(2)-symmetric core units of interest as candidates for HIV protease inhibition. Addition of unbranched and branched organolithium reagents to cyanohydrins from l-phenylalaninal and l-isoleucinal, followed by in situ reduction of the intermediate imines and CHT deprotection under MW irradiation, led to 1,3-diamino alcohols 6a and 8a as the major products in satisfactory to good yields. The first preparation of a previously unreported pseudo-C(2)-symmetric triamino derivative was accomplished expeditiously via high-yielding nitro-Mannich addition of the silylnitronate, from 2-phenyl-1-nitroethane, to the PMP imine derived from l-phenylalaninal. Reduction of the nitro group in the moderately unstable nitro diamine adduct, followed by chromatographic separation of the required diastereoisomer and CHT debenzylation under MW irradiation, led to the 2-PMP-protected triamine 19 isolated as a bis(sulfonamide).
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Banco de datos:
MEDLINE
Asunto principal:
Compuestos Organometálicos
/
Inhibidores de la Proteasa del VIH
/
Técnicas Químicas Combinatorias
/
Amino Alcoholes
/
Litio
Idioma:
En
Revista:
J Org Chem
Año:
2003
Tipo del documento:
Article
País de afiliación:
Italia