Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin.
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.
Feldman
Ken S.
KS
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802.
Smith
Randall S.
RS