Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B.
A stereoselective synthesis of 7-dihydro-triocacarcinose B, a branched octose from the quinocyclines, has been achieved. The biocatalytic resolution of a Baylis-Hillman adduct and a subsequent ring-closing metathesis were used to assemble the molecular framework. Subsequent key steps were a highly stereoselective epoxidation and a regio- and stereoselective opening of the epoxide by allyl alcohol and HClO4 to introduce the C(3)-OH group in protected form. The 7-dihydro-triocacarcinose B could be converted into the corresponding 1,7-anhydrosugar.
König
Christian M
CM
Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, Marburg, Germany.
Harms
Klaus
K
Koert
Ulrich
U
D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009930:Organic Chemicals / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D009005:Monosaccharides; D009930:Organic Chemicals; C524836:methyl 7-dihydro-trioxacarcinoside B; D006859:Hydrogen