Synthesis of an Orthogonally Protected Polyhydroxylated Cyclopentene from l-Sorbose.
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).
School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland. daniele.lore@irbbarcelona.org.
Daniele
http://orcid.org/0000-0002-6068-5975
D
Lo Re
School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland.
Leigh
L
Jones
Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, C/Baldiri Reixac 10, Barcelona, E-08028, Spain.|Department of Organic Chemistry, University of Barcelona, Marti i Franques 1-11, Barcelona, E-08028, Spain.
Ernest
E
Giralt
School of Chemistry, National University of Ireland, Galway, University Road, Galway, Ireland. paul.v.murphy@nuigalway.ie.
Paul
P
Murphy
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D006900:Hydroxylation; D008968:Molecular Conformation; D013013:Sorbose / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D003517:Cyclopentanes; D013013:Sorbose
carbohydrates; chiral pool; glycomimetics; multidrug resistance; orthogonal protection