Serial Radical Cyclization of Branched Carbohydrates. 2. Claisen Rearrangement Routes to Muliply Substituted Pyranoside Diquinanes

Article abstract of DOI:10.1021/jo00283a034

Pyranosidic diquinanes, which may be prepared by serial radical cyclization of suitably functionalized alkyl residues at C2 and C3, are potential precursors for polyquinane synthesis.The residues at C3 are installed via a Claisen rearrangement, and it is therefore possible to obtain more highly substituted diquinane synthons by incorporating methyl residues at the appropriate sites in the precursors.The consequences of these substituents on the stereoselectivity of the Claisen rearrangement have been examined.