title: The Synthesis of Both Diastereomers of 5'-Methylhomoaristeromycin.
abstract: The preparation of the C-5' diastereomers of 5'-homoaristeromycin has been achieved in 6 steps beginning with readily available (3aR,6aR)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[1,3]dioxol-4-one in a Michael reaction employing chiral Evans N-acyloxazolidinones that served to direct the requisite side chain stereochemistry. The two targets were evaluated against a battery of viruses and found to possess activity only towards yellow fever. Both compounds were non-cytotoxic.
authors.affiliation: a Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University , Auburn , Alabama 36849.
authors.forename: Wei
authors.initials: W
authors.lastname: Ye
authors.affiliation: a Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University , Auburn , Alabama 36849.
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008745:Methylation; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014025:Titanium / Q000737:chemistry; D014777:Virus Diseases / Q000188:drug therapy; D014780:Viruses / Q000187:drug effects
chemical_list: C500020:5'-homoaristeromycin; D000998:Antiviral Agents; D023303:Oxazolidinones; D014025:Titanium; D000241:Adenosine
keywords: C-5′ extended aristeromycins; Carbocyclic nucleosides; Evans chiral auxiliary; N-acyloxazolidinones; titanium enolates