Enantioselective total synthesis of (-)-Salinosporamide A (NPI-0052) |
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| Authors: | Ling Taotao Macherla Venkat R Manam Rama Rao McArthur Katherine A Potts Barbara C M |
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| Institution: | Nereus Pharmaceuticals, Inc., 10480 Wateridge Circle, San Diego, California 92121, USA. |
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| 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. |
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