Synthesis of an orthogonally protected polyhydroxylated cyclopentene from l-Sorbose
Abstract© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim 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).
CitationJones, L., Lo Re, D., Giralt, E., & Murphy, P. (2016). Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose. Chemistry - An Asian Journal , 11(14), 2035- 2040. https://doi.org/10.1002/asia.201600736
JournalChemistry - An Asian Journal
SponsorsThis work was supported by Science Foundation Ireland (grant Nos. 07/IN.1/B966 and 11/TIDA/B2047). The research leading to these results also received funding from the People Programme (Marie Curie Actions) of the European Union's Seventh Framework Programme (FP7/2007–2013) under grant agreement number PIEF‐GA‐2011‐299042 and from the European Union's Seventh Framework Programme for research, technological development and demonstration under grant agreement no 600404 and from MINECO‐FEDER (Bio2013‐40716‐R). IRB Barcelona is the recipient of a Severo Ochoa Award of Excellence from MINECO (Government of Spain).
Except where otherwise noted, this item's license is described as https://creativecommons.org/licenses/by-nc-nd/4.0/
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