Total Synthesis of Salinosporamide A
- 19 May 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (23) , 8298-8299
- https://doi.org/10.1021/ja0522783
Abstract
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).Keywords
This publication has 14 references indexed in Scilit:
- Total Synthesis of (±)-Jiadifenin, a Non-peptidyl Neurotrophic ModulatorJournal of the American Chemical Society, 2004
- Total Synthesis of TMC-95A and -B via a New Reaction Leading to Z-Enamides. Some Preliminary Findings as to SARJournal of the American Chemical Society, 2004
- A Simple Stereocontrolled Synthesis of Salinosporamide AJournal of the American Chemical Society, 2004
- Simplified Synthetic TMC‐95A/B Analogues Retain the Potency of Proteasome Inhibitory ActivityChemBioChem, 2003
- Salinosporamide A: A Highly Cytotoxic Proteasome Inhibitor from a Novel Microbial Source, a Marine Bacterium of the New Genus SalinosporaAngewandte Chemie International Edition in English, 2003
- New methods and reagents in organic synthesis. 83. Stereoselective total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77Journal of the American Chemical Society, 1989
- A formal total synthesis of (±)-strigolTetrahedron Letters, 1987
- Conversion of L-pyroglutamic acid to 4-alkyl-substituted L-prolines. The synthesis of trans-4-cyclohexyl-L-prolineThe Journal of Organic Chemistry, 1986
- A periodonium trifluoromethanesulfonate. An isolable 10-I-4 organoiodine speciesJournal of the American Chemical Society, 1982
- A stereospecific total synthesis of (.+-.)-methylenomycin A and its epimer, (.+-.)-epimethylenomycin AJournal of the American Chemical Society, 1980