Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide

Research output: Contribution to journal › Journal article › Research › peer-review

Standard

Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide. / Doan, Thi Quynh Nhu; Crestey, François; Olsen, Carl Erik; Christensen, Søren Brøgger.

In: Journal of Natural Products, Vol. 78, No. 6, 2015, p. 1406-1414.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Doan, TQN, Crestey, F, Olsen, CE & Christensen, SB 2015, 'Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide', Journal of Natural Products, vol. 78, no. 6, pp. 1406-1414. https://doi.org/10.1021/acs.jnatprod.5b00333

APA

Doan, T. Q. N., Crestey, F., Olsen, C. E., & Christensen, S. B. (2015). Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide. Journal of Natural Products, 78(6), 1406-1414. https://doi.org/10.1021/acs.jnatprod.5b00333

Vancouver

Doan TQN, Crestey F, Olsen CE, Christensen SB. Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide. Journal of Natural Products. 2015;78(6):1406-1414. https://doi.org/10.1021/acs.jnatprod.5b00333

Author

Doan, Thi Quynh Nhu ; Crestey, François ; Olsen, Carl Erik ; Christensen, Søren Brøgger. / Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide. In: Journal of Natural Products. 2015 ; Vol. 78, No. 6. pp. 1406-1414.

Bibtex

@article{26b1793be0fd4dcea053291c33e3b980,
title = "Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide",
abstract = "The difference of reactivity of the hexaoxygenated natural product thapsigargin (1) and the pentaoxygenated nortrilobolide (3) is compared in order to develop a chemo- and regioselective method for the conversion of nortrilobolide (3) into the natural product 2-acetoxytrilobolide (4). For the first time, a stereoselective synthesis of the 2-acetoxytrilobolide (4) is described, which involves two key reactions: the first chemical step is a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone. The second process consists of a stereoselective α´-acyloxylation of the key intermediate α,β-unsaturated ketone to afford its corresponding acetoxyketone, which was converted into 2-acetoxytrilobolide (4) in a few steps. This innovative approach would allow the synthesis of a broad library of novel and valuable penta- and hexaoxygenated guaianolides as potential anticancer agents.",
author = "Doan, {Thi Quynh Nhu} and Fran{\c c}ois Crestey and Olsen, {Carl Erik} and Christensen, {S{\o}ren Br{\o}gger}",
year = "2015",
doi = "10.1021/acs.jnatprod.5b00333",
language = "English",
volume = "78",
pages = "1406--1414",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "6",

}

RIS

TY - JOUR

T1 - Chemo- and regioselective functionalization of nortrilobolide: application for semi-synthesis of the natural product 2-acetoxytrilobolide

AU - Doan, Thi Quynh Nhu

AU - Crestey, François

AU - Olsen, Carl Erik

AU - Christensen, Søren Brøgger

PY - 2015

Y1 - 2015

N2 - The difference of reactivity of the hexaoxygenated natural product thapsigargin (1) and the pentaoxygenated nortrilobolide (3) is compared in order to develop a chemo- and regioselective method for the conversion of nortrilobolide (3) into the natural product 2-acetoxytrilobolide (4). For the first time, a stereoselective synthesis of the 2-acetoxytrilobolide (4) is described, which involves two key reactions: the first chemical step is a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone. The second process consists of a stereoselective α´-acyloxylation of the key intermediate α,β-unsaturated ketone to afford its corresponding acetoxyketone, which was converted into 2-acetoxytrilobolide (4) in a few steps. This innovative approach would allow the synthesis of a broad library of novel and valuable penta- and hexaoxygenated guaianolides as potential anticancer agents.

AB - The difference of reactivity of the hexaoxygenated natural product thapsigargin (1) and the pentaoxygenated nortrilobolide (3) is compared in order to develop a chemo- and regioselective method for the conversion of nortrilobolide (3) into the natural product 2-acetoxytrilobolide (4). For the first time, a stereoselective synthesis of the 2-acetoxytrilobolide (4) is described, which involves two key reactions: the first chemical step is a one-pot substitution-oxidation reaction of an allylic ester into its corresponding α,β-unsaturated ketone. The second process consists of a stereoselective α´-acyloxylation of the key intermediate α,β-unsaturated ketone to afford its corresponding acetoxyketone, which was converted into 2-acetoxytrilobolide (4) in a few steps. This innovative approach would allow the synthesis of a broad library of novel and valuable penta- and hexaoxygenated guaianolides as potential anticancer agents.

U2 - 10.1021/acs.jnatprod.5b00333

DO - 10.1021/acs.jnatprod.5b00333

M3 - Journal article

C2 - 26078214

VL - 78

SP - 1406

EP - 1414

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 6

ER -

ID: 138930838