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Stereoselective synthesis of methyl 7-dihydro-trioxacarcinoside B
Christian M König1, Klaus Harms, Ulrich Koert
1Fachbereich Chemie, Philipps-University Marburg, Hans-Meerwein-Strasse, Marburg, Germany.
Abstract:
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.
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