Total synthesis of dendroamide a: oxazole and thiazole construction using an oxodiphosphonium salt.
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.
You
Shu-Li
SL
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.
Kelly
Jeffery W
JW
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D008956:Models, Chemical; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry*
D000596:Amino Acids; D009943:Organophosphorus Compounds; D010080:Oxazoles; D010455:Peptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C100903:dendroamide A