943542-51-6Relevant articles and documents
Enantioselective total synthesis of (-)-salinosporamide A (NPI-0052)
Ling, Taotao,Macherla, Venkat R.,Manam, Rama Rao,McArthur, Katherine A.,Potts, Barbara C. M.
, p. 2289 - 2292 (2008/02/05)
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.