Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols.
Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-alpha-D-glucopyranoside and methyl 4,6-O-benzylidene-alpha-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus.
Rauter
Amélia P
AP
Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Ed. C8, 5 degrees Piso, Campo Grande, 1749-016 Lisboa, Portugal. aprauter@fc.ul.pt
Piedade
Fátima
F
Almeida
Tânia
T
Ramalho
Rui
R
Ferreira
Maria J
MJ
Resende
Ricardo
R
Amado
Joana
J
Pereira
Helena
H
Justino
Jorge
J
Neves
Ana
A
Silva
Filipa V M
FV
Canda
Tana
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D018360:Crystallography, X-Ray; D003500:Cyclization; D019281:Dimerization; D005947:Glucose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D006018:Glycols / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000494:pharmacology; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D006018:Glycols; D007783:Lactones; D047028:Macrocyclic Compounds; D011726:Pyridinium Compounds; C111019:pyridinium chlorochromate; D005947:Glucose