Total synthesis of salinosporamide A.
Total synthesis of potent proteasome inhibitor salinosporamide A (1) has been accomplished, which features strictly substrate-controlled operations starting with the only chiral center of (R)-pyroglutamic acid. The consecutive quaternary carbons within 1 have been efficiently constructed by manipulation of two intramolecular reactions: (1) carbonate-mediated internal acylation of imidate ester (4 --> 14) and (2) selenocyclization of aldehyde to exocyclic methylene group (5 --> 18).
Endo
Atsushi
A
Laboratory for Bioorganic Chemistry, Sloan-Kettering Institute for Cancer Research, 1275 York Avenue, New York, NY 10021, USA.
Danishefsky
Samuel J
SJ
D000192:Actinomycetales / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis*; D011480:Protease Inhibitors / Q000138:chemical synthesis; D011758:Pyrroles / Q000138:chemical synthesis*; D012643:Selenium / Q000737:chemistry; D013237:Stereoisomerism
D007783:Lactones; D011480:Protease Inhibitors; D011758:Pyrroles; C475865:marizomib; D012643:Selenium