Bicyclic beta-Hydroxytetrahydrofurans as precursors of medium ring keto-lactones.
The reaction of a series of cis-fused bicyclic beta-hydroxytetrahydrofurans with ruthenium tetraoxide, generated in situ from ruthenium trichloride and sodium periodate, afforded 9- and 10-membered keto-lactones in moderate to good yields, in a clean and straightforward fashion. The starting beta-hydroxyethers were obtained from the corresponding 3-alkenols by two alternative procedures, depending on their pattern of substitution: (a) epoxidation by dimethyldioxirane, followed by base-catalyzed cyclization of the resulting epoxyalcohol, and (b) thallium trinitrate-mediated cyclization of the 3-alkenols, a method already described by our group.
Ferraz
Helena M C
HM
Instituto de Química, Universidade de São Paulo, CP 26077, CEP 05513-970, São Paulo, SP, Brazil. hmferraz@iq.usp.br
Longo
Luiz S
LS
D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D005663:Furans; D007783:Lactones