A complete asymmetric synthesis of polyhydroxypiperidines |
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| Authors: | Hyunsoo Han |
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| Institution: | Department of Chemistry, The University of Texas at San Antonio, 6900 N. Loop 1604 West, San Antonio, TX 78249, USA |
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| Abstract: | A new general methodology for the asymmetric synthesis of polyhydroxypiperidines is described. The readily available achiral olefin 4 was transformed to 5-des(hydroxymethyl)-1-deoxynojirimycin (1) and its mannose analog 10 via regioselective aminohydroxylation (AA), ring-closing metathesis (RCM), and diastereoselective dihydroxylation reactions. Thus, the developed methodology made it possible to install all stereocenters in 1 and 10 in a highly stereocontrolled fashion. |
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| Keywords: | polyhydroxypiperidine regioselective aminohydroxylation ring-closing metathesis |
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