An enantioselective enzymatic desymmetrization route to hexahydro-4H-furopyranol,a high-affinity ligand for HIV-1 protease inhibitors |
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Authors: | Arun K. Ghosh Anindya Sarkar |
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Affiliation: | Department of Chemistry and Department of Medicinal Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907, United States |
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Abstract: | An enantioselective synthesis of (3aS,4S,7aR)-hexahydro-4H-furo[2,3-b]pyran-4-ol, a high-affinity nonpeptide ligand for a variety of potent HIV-1 protease inhibitors is described. The key steps involved a highly enantioselective enzymatic desymmetrization of meso-diacetate, an efficient transacetalization, and a highly diastereoselective reduction of a ketone. This route is amenable to large-scale synthesis using readily available starting materials. |
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Keywords: | Enzymatic hydrolysis Enantioselective Desymmetrization HIV-1 protease inhibitors Ligand |
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