(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

Claire L. Arthurs; Katharine F. Lingley; Michela Piacenti; Ian J. Stratford; Tanja Tatic; Roger C. Whitehead; Natasha S. Wind

doi:10.1016/j.tetlet.2008.02.059

(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

Claire L. Arthurs, Katharine F. Lingley, Michela Piacenti, Ian J. Stratford, Tanja Tatic, Roger C. Whitehead, Natasha S. Wind

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

Abstract

Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (-)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented. © 2008 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	2410-2413
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2008.02.059
Publication status	Published - 7 Apr 2008

Keywords

Anti-cancer
Cyclopropane
Natural product
Quinic acid

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tetlet.2008.02.059

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Arthurs, C. L., Lingley, K. F., Piacenti, M., Stratford, I. J., Tatic, T., Whitehead, R. C., & Wind, N. S. (2008). (-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties. Tetrahedron Letters, 49(15), 2410-2413. https://doi.org/10.1016/j.tetlet.2008.02.059

@article{7367a0398912407cb9376541c2bf7c1a,

title = "(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties",

abstract = "Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (-)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented. {\textcopyright} 2008 Elsevier Ltd. All rights reserved.",

keywords = "Anti-cancer, Cyclopropane, Natural product, Quinic acid",

author = "Arthurs, {Claire L.} and Lingley, {Katharine F.} and Michela Piacenti and Stratford, {Ian J.} and Tanja Tatic and Whitehead, {Roger C.} and Wind, {Natasha S.}",

year = "2008",

month = apr,

day = "7",

doi = "10.1016/j.tetlet.2008.02.059",

language = "English",

volume = "49",

pages = "2410--2413",

journal = "Tetrahedron Letters",

issn = "1873-3581",

publisher = "Elsevier BV",

number = "15",

}

Arthurs, CL, Lingley, KF, Piacenti, M, Stratford, IJ, Tatic, T, Whitehead, RC & Wind, NS 2008, '(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties', Tetrahedron Letters, vol. 49, no. 15, pp. 2410-2413. https://doi.org/10.1016/j.tetlet.2008.02.059

(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties. / Arthurs, Claire L.; Lingley, Katharine F.; Piacenti, Michela et al.
In: Tetrahedron Letters, Vol. 49, No. 15, 07.04.2008, p. 2410-2413.

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

TY - JOUR

T1 - (-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

AU - Arthurs, Claire L.

AU - Lingley, Katharine F.

AU - Piacenti, Michela

AU - Stratford, Ian J.

AU - Tatic, Tanja

AU - Whitehead, Roger C.

AU - Wind, Natasha S.

PY - 2008/4/7

Y1 - 2008/4/7

N2 - Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (-)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented. © 2008 Elsevier Ltd. All rights reserved.

AB - Syntheses of three novel analogues of the Streptomyces metabolite COTC are described, using the versatile chiral pool starting material, (-)-quinic acid. The results of bioassays of the target compounds against two lung cancer cell lines, A549 and H460, are presented. © 2008 Elsevier Ltd. All rights reserved.

KW - Anti-cancer

KW - Cyclopropane

KW - Natural product

KW - Quinic acid

U2 - 10.1016/j.tetlet.2008.02.059

DO - 10.1016/j.tetlet.2008.02.059

M3 - Article

SN - 1873-3581

VL - 49

SP - 2410

EP - 2413

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

(-)-Quinic acid: a versatile precursor for the synthesis of analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) which possess anti-tumour properties

Abstract

Keywords

UN SDGs

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