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Synthesis of an Orthogonally Protected Polyhydroxylated Cyclopentene from l ‐Sorbose
Author(s) -
Lo Re Daniele,
Jones Leigh,
Giralt Ernest,
Murphy Paul
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600736
Subject(s) - cyclopentene , hela , chemistry , regioselectivity , hydrolysis , glycoside , stereochemistry , organic chemistry , biochemistry , cell , catalysis
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).