Synthesis of an Orthogonally Protected Polyhydroxylated Cyclopentene from l‐Sorbose |
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Authors: | Dr Daniele Lo Re Dr Leigh Jones Prof Ernest Giralt Prof Paul Murphy |
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Institution: | 1. School of Chemistry, National University of Ireland, Galway, Galway, Ireland;2. Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Barcelona, Spain;3. Department of Organic Chemistry, University of Barcelona, Barcelona, Spain |
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Abstract: | The use of l ‐sorbose in the synthesis of functionalized cyclopentene derivatives was accomplished. These cyclopentene derivatives are related to those found in naturally occurring jatrophane frameworks and in other bioactive compounds. The formation of allyl α‐l ‐sorbopyranoside was a key synthetic step. Regioselective introduction of protecting groups was followed by the hydrolysis of the allyl glycoside to furnish a fully protected acyclic l ‐sorbose derivative. This acyclic intermediate was subsequently used to give an orthogonally protected polyhydroxylated cyclopentene, which has potential for further synthesis of bioactive compounds. The protected cyclopentene itself showed a clear cytotoxic activity when tested against a panel of human cancer cell lines (HT29, LS174T, SW620, A549, and HeLa cells). |
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Keywords: | carbohydrates chiral pool glycomimetics multidrug resistance orthogonal protection |
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