Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose.
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In: Chemistry - An Asian Journal , Vol. 11, No. 14, 20.07.2016, p. 2035-2040.
Research output: Contribution to journal › Article › peer-review
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TY - JOUR
T1 - Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose.
AU - Jones, Leigh
AU - Lo Re, Daniel
AU - Giralt, Ernest
AU - Murphy, Paul
PY - 2016/7/20
Y1 - 2016/7/20
N2 - 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).
AB - 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).
U2 - 10.1002/asia.201600736
DO - 10.1002/asia.201600736
M3 - Article
VL - 11
SP - 2035
EP - 2040
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-471X
IS - 14
ER -