640722-90-3Relevant academic research and scientific papers
Total Synthesis of Dendroamide A: Oxazole and Thiazole Construction Using an Oxodiphosphonium Salt
You, Shu-Li,Kelly, Jeffery W.
, p. 9506 - 9509 (2007/10/03)
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.
