title: Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052).
abstract: A novel enantioselective total synthesis of 20S proteasome inhibitor Salinosporamide A (NPI-0052; 1) is presented. Key features include intramolecular aldol cyclization of 6 to simultaneously generate the three chiral centers of advanced intermediate 5, cyclohexene ring addition using B-2-cyclohexen-1-yl-9-BBN, and inversion of the C-5 stereocenter by oxidation followed by enantioselective enzymatic reduction.
authors.affiliation: Nereus Pharmaceuticals, Inc., 10480 Wateridge Circle, San Diego, California 92121, USA.
authors.forename: Taotao
authors.initials: T
authors.lastname: Ling
authors.forename: Venkat R
authors.initials: VR
authors.lastname: Macherla
authors.forename: Rama Rao
authors.initials: RR
authors.lastname: Manam
authors.forename: Katherine A
authors.initials: KA
authors.lastname: McArthur
authors.forename: Barbara C M
authors.initials: BC
authors.lastname: Potts
mesh_terms: D018360:Crystallography, X-Ray; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D011758:Pyrroles; C475865:marizomib