title: Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin.
abstract: The biomimetic synthesis of pedunculagin (1) was accomplished through the sequential diastereoselective formation of two biphenyl C-C bonds. The synthesis strategy employed is predicated on extensive conformational modeling and involves initial oxidative coupling of the galloyl moieties at the O(2) and O(3) positions of an appropriately protected glucose-derived core, followed by installation and oxidative coupling of galloyl esters at the O(4) and O(6) positions.
authors.affiliation: Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802.
authors.forename: Ken S.
authors.initials: KS
authors.lastname: Feldman
authors.forename: Randall S.
authors.initials: RS
authors.lastname: Smith