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Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-Sorbose

Lo Re, Daniele
; 
Jones, Leigh F.
; 
Giralt, Ernest
; 
Murphy, Paul V.
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Publication Date
2016-07-06
Keywords
Carbohydrates, Chiral pool, Glycomimetics, Multidrug resistance, Orthogonal protection, Jatrophane Diterpenes, P-Glycoprotein, (2r,3r)-disubstituted tetrahydropyrans, Antiproliferative activity, Biological evaluation, Multidrug-resistance, Acid derivatives, Allyl ethers, Tumor cells, Inhibitors
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Lo Re, Daniele, Jones, Leigh, Giralt, Ernest, & Murphy, Paul. (2016). Synthesis of an Orthogonally Protected Polyhydroxylated Cyclopentene from l-Sorbose. Chemistry – An Asian Journal, 11(14), 2035-2040. doi: 10.1002/asia.201600736
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 -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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Publisher
Chemical Editorial Society (ACES) / Wiley
Publisher DOI
10.1002/asia.201600736
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Attribution-NonCommercial-NoDerivs 3.0 Ireland
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School of Chemistry (Scholarly Articles)