Dipeptide isosteres. 1. Synthesis of dihydroxyethylene dipeptide isosteres via diastereoselective additions of alkyllithium reagents to N,N-dimethylhydrazones. Preparation of renin and HIV-1 protease inhibitor transition-state mimics

Autor:	Stephen Condon, William R. Baker
Rok vydání:	1993
Předmět:	chemistry.chemical_classification Dipeptide Nucleophilic addition biology Stereochemistry Organic Chemistry Hydrazone Ether Aldehyde chemistry.chemical_compound chemistry HIV-1 protease biology.protein Amine gas treating Protecting group
Zdroj:	The Journal of Organic Chemistry. 58:3277-3284
ISSN:	1520-6904 0022-3263
Popis:	The amino and diamino dihydroxyethylene dipeptide isosteres 19a,b and 23 are important intermediates for the preparation of inhibitors of human renin and HIV-1 protease, respectively. A general synthetic strategy was developed to access both dipeptide isosteres. The key step was a diastereoselective addition of an alkyllithium reagent to an aldehyde hydrazone. Thus, isosteres 19a and 19b were synthesized by addition of either benzyllithium or (cyclohexylmethyl)lithium to (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-formyl-1,3-dioxolane N,N-dimethylhydrazone (4) in dietbyl ether at -10 o C. The hydrazine addition product was reduced to the amine, and the acetonide protecting group was removed
Databáze:	OpenAIRE
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