A concise formal total synthesis of TMC-95A/B proteasome inhibitors.
[reaction: see text] A formal total synthesis of proteasome inhibitors TMC-95A/B is described. The synthesis features a stereoselective modified Julia olefination and a diastereoselective dihydroxylation to construct the highly oxidized tryptophan residue.
Albrecht
Brian K
BK
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Williams
Robert M
RM
D003500:Cyclization; D003546:Cysteine Endopeptidases; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors*; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D046988:Proteasome Endopeptidase Complex; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives / Q000138:chemical synthesis
D004791:Enzyme Inhibitors; D009097:Multienzyme Complexes; D010456:Peptides, Cyclic; C408291:TMC-95A; C408292:TMC-95B; D014364:Tryptophan; D003546:Cysteine Endopeptidases; D046988:Proteasome Endopeptidase Complex