An approach to the total synthesis of sinefungin.
AUTOR(ES)
Mock, G A
RESUMO
Condensation of N6-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde with nitromethane followed by acid catalyzed acetylation and borohydride reduction leads to N6-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-6-nitro-beta-D-ribo-hexofuranosyl)adenine (4). A second nitroaldol condensation between 4 and N-benzyloxycarbonly-L-aspartic acid-beta-semialdehyde alpha-benzyl ester (5) followed by acetylation and borohydride reduction leads to a fully protected 6'-nitro modification of sinefungin and its C6'-epimer (7). Hydrolysis of the acetonide followed by sequential reduction of the benzyl derived protecting groups and the nitro group and debenzoylation leads to a modest yield of a 3:1 mixture of sinefungin (1) and 6'-episinefungin which can only be separated by analytical ion exchange chromatography.
ACESSO AO ARTIGO
http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=326912Documentos Relacionados
- Molecular target of the antileishmanial action of sinefungin.
- An approach to the construction of the carbon skeleton of marine nor-sesquiterpenes. Total synthesis of (±)-dehalo-napalilactone
- A unified approach to the tedanolides: Total synthesis of (+)-13-deoxytedanolide
- An approach to the synthesis of thioesters and selenoesters promoted by Rongalite®
- An approach to the stereoselective synthesis of Sp-dinucleoside phosphorothioates using phosphotriester chemistry.