Synthesis of 10 stereochemically distinct bis-tetrahydrofuran intermediates for creating a library of 64 asimicin stereoisomers |
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Authors: | Zhiyong Chen |
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Institution: | The Skaggs Institute for Chemical Biology and The Department of Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, United States |
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Abstract: | Stereoselective synthesis of 10 unique bifunctional stereoisomeric adjacent bis-THF intermediates (R = Bz), including 5.1-5.4, 5.7-5.9, 5.11, and 5.15-5.16, of 16 possible compounds, is described. The key steps used in the synthesis of these compounds included the rhenium(VII) oxide-mediated and the Co(modp)2-catalyzed trans oxidative cyclizations (OCs), the OsO4-catalyzed cis OC, and the Williamson’s type etherification reactions. The remaining six bis-THF intermediates (R = Bn) can be prepared from 5.7-5.9, 5.11, and 5.15-5.16 (R = Bz) in two steps, including protection of the free alcohol as benzyl ether followed by the benzoate deprotection. These intermediates should provide access to all 64 asimicin stereoisomers and their analogs. |
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