Stereoselective synthesis of (+)-boronolide and (−)-5-epi-boronolide |
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| Affiliation: | 1. National Energy Technology Laboratory, Pittsburgh, PA 15236, USA;2. AECOM, P.O. Box 618, South Park, PA 15129, USA;3. Etch Product Group, LAM Research Corporation, 4400 Cushing Parkway, Fremont, CA 94539, USA;4. Department of Physics, North Carolina State University, Raleigh, NC 27695. USA;5. Department of Chemistry, Surface Science Center, University of Pittsburgh, Pittsburgh, PA 15261, USA;6. Department of Chemical and Petroleum Engineering, University of Pittsburgh, Pittsburgh, PA 15261, USA |
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| Abstract: | Stereoselective synthesis of boronolide and 5-epi-boronolide was achieved from d-(−)-tartaric acid. The key step involves the reduction of a keto Weinreb amide for the synthesis of boronolide, and a single pot construction of a diketone from the bis-Weinreb amide of tartaric acid and subsequent reduction with L-Selectride for 5-epi-boronolide. |
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