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Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose.

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Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose. / Jones, Leigh; Lo Re, Daniel; Giralt, Ernest et al.
In: Chemistry - An Asian Journal , Vol. 11, No. 14, 20.07.2016, p. 2035-2040.

Research output: Contribution to journal › Article › peer-review

HarvardHarvard

Jones, L, Lo Re, D, Giralt, E & Murphy, P 2016, 'Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose.', Chemistry - An Asian Journal , vol. 11, no. 14, pp. 2035-2040. https://doi.org/10.1002/asia.201600736

APA

Jones, 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

CBE

Jones 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

MLA

Jones, Leigh et al. "Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose.". Chemistry - An Asian Journal . 2016, 11(14). 2035-2040. https://doi.org/10.1002/asia.201600736

VancouverVancouver

Jones L, Lo Re D, Giralt E, Murphy P. Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose. Chemistry - An Asian Journal . 2016 Jul 20;11(14):2035-2040. Epub 2016 Jul 6. doi: 10.1002/asia.201600736

Author

Jones, Leigh ; Lo Re, Daniel ; Giralt, Ernest et al. / Synthesis of an orthogonally protected polyhydroxylated cyclopentene from L-sorbose. In: Chemistry - An Asian Journal . 2016 ; Vol. 11, No. 14. pp. 2035-2040.

RIS

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 -