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Total Synthesis of Dendroamide A:  Oxazole and Thiazole Construction Using an Oxodiphosphonium Salt

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journal contribution
posted on 28.11.2003, 00:00 authored by Shu-Li You, Jeffery W. Kelly
The total synthesis of dendroamide A (1), a multidrug-resistance reversing bistratamide-type peptide-derived macrocycle, has been accomplished in 19% yield. Fmoc-protected amino acids were condensed into appropriately protected dipeptides which were treated with bis(triphenyl)oxodiphosphonium trifluoromethanesulfonate to afford oxazoles and thiazolines (oxidized to thiazoles) with high chemo- and stereoselectivity. The convergent condensation of three heterocyclic amino acids followed by macrocyclization afforded the natural product.