Highly stereoselective synthesis of aristeromycin through dihydroxylation of 4-aryl-1-azido-2-cyclopentenes.
J Org Chem
; 69(3): 655-9, 2004 Feb 06.
Article
en En
| MEDLINE
| ID: mdl-14750788
ABSTRACT
Dihydroxylation of 4-aryl-1-azido-2-cyclopentenes 6, in which an aryl group is used as a synthetic equivalent of CH(2)OH, was studied to improve the low to moderate stereoselectivity previously reported for cyclopentenes 3 possessing CH(2)X and nitrogen atom-containing groups. 2-Furyl, Ph, and p-MeOC(6)H(4) groups were chosen as the aryl groups. Compounds 6a-c possessing such aryl groups were prepared by CuCN-catalyzed reaction between 2-cyclopentene-1,4-diol monoacetate 9 and the corresponding Grignard reagents followed by substitution of the hydroxyl group with (PhO)(2)P(=O)N(3). The desired diols 7a-c were obtained with higher selectivities of >71 when dihydroxylation of 6a-c was carried out at 0 degrees C with OsO(4) (catalyst) and NMO in a mixed solvent of MeCN, THF, t-BuOH, and H(2)O. Among them, the furyl compound recorded the highest selectivity of 141. The furyl and azido groups on diol 7a were converted into hydroymethyl and adeninyl groups, respectively, to produce acetonide 2, which upon hydrolysis affords aristeromycin 1.
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Bases de datos:
MEDLINE
Asunto principal:
Azidas
/
Derivados del Benceno
/
Adenosina
/
Ciclopentanos
Idioma:
En
Revista:
J Org Chem
Año:
2004
Tipo del documento:
Article
País de afiliación:
Japón