title: A concise, total synthesis of the TMC-95A/B proteasome inhibitors.
abstract: A concise, total synthesis of the proteasome inhibitors TMC-95A/B has been accomplished. The synthesis features the use of an L-serine-derived E-selective modified Julia olefination reaction to ultimately control the stereochemical outcome of the highly oxidized tryptophan fragment. Additionally, the limited use of protecting groups at a late stage of the total synthesis allowed for its completion in an efficient manner.
authors.affiliation: Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
authors.forename: Brian K
authors.initials: BK
authors.lastname: Albrecht
authors.forename: Robert M
authors.initials: RM
authors.lastname: Williams
mesh_terms: D002625:Chemistry, Organic / Q000379:methods; D003546:Cysteine Endopeptidases; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors*; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011480:Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D046988:Proteasome Endopeptidase Complex; D013237:Stereoisomerism
chemical_list: D009097:Multienzyme Complexes; D010456:Peptides, Cyclic; D011480:Protease Inhibitors; C408291:TMC-95A; C408292:TMC-95B; D003546:Cysteine Endopeptidases; D046988:Proteasome Endopeptidase Complex