ja0522783_si_001.pdf (813.82 kB)
Total Synthesis of Salinosporamide A
journal contribution
posted on 2005-06-15, 00:00 authored by Atsushi Endo, Samuel J. DanishefskyTotal 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).