A versatile approach toward the ansamycin antibiotics.
The ansamycin antibiotics contain metacyclophanic macrolactams, many of which possess potent antitumor activity. Only a few total syntheses of this family of natural products have been reported, and modifications to increase potency have not been described. Therefore, a method was developed to prepare the trienomycin A core via resin-bound triphenylphosphonium salts, which serve as both a reagent and a traceless linker to afford olefinic products that undergo ring-closing metathesis (RCM) to give macrocyclic scaffolds of varying ring sizes.
Peng
Weimin
W
Department of Medicinal Chemistry and The Center for Chemical Methodology and Library Development, The University of Kansas, 1251 Wescoe Hall Drive, Malott 4070, Lawrence, Kansas 66045-7562, USA.
Blagg
Brian S J
BS
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007097:Imines / Q000737:chemistry*; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D017828:Rifabutin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007097:Imines; D047029:Lactams, Macrocyclic; D009942:Organometallic Compounds; D017828:Rifabutin; D012238:Rhodium