Dr Joelle Prunet

Senior Lecturer (School of Chemistry)

telephone: 01413308774
email: Joelle.Prunet@glasgow.ac.uk

School of Chemistry, Joseph Black Building - A4-13, University Avenue, Glasgow G12 8QQ

Research interests

Research Interests

The main research interest of The Prunet Group is the synthesis of biologically active natural products, such as taxol, a powerful antitumor agent, or dolabelide C and hexacyclinic acid, molecules with cytotoxic activity. In our approaches towards the target molecules, we uncover problems that cannot be easily solved by known reactions, and to overcome these difficulties we try to develop new methodologies that can also be applied to other syntheses.

‌‌ Joelle Prunet - Taxol

Publication Highlights

Gamba-Canchez, D.; Prunet, J. J. Org. Chem. 2010, 75, 3129-3132 Synthesis of Modified Methyl Furanosides by Intramolecular Oxa-Michael Reaction followed by Pummerer Rearrangement.
Ma, C.; Schiltz, S.; Le Goff, Xavier F.; Prunet, J. Chem. Eur. J. 2008, 7314-7323 Ring-Closing Metathesis in the Synthesis of BC Ring-Systems of Taxol.
Toueg, J.; Prunet J. Org. Lett. 2008, 10, 45-48 Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition: Study towards the Synthesis of the ABC Ring-System of Hexacyclinic Acid.
Rotulo-Sims, D.; Prunet J. Org. Lett. 2007, 9, 4147-4150 Tandem Conjugate Addition-Elimination for the Diastereoselective Synthesis of 4E-Alkenyl Syn 1,3-Diols.
Vincent, A.; Prunet, J. Synlett 2006, 2269-2271 Enantioselective Synthesis of the C1-C15 Fragment of Dolabelide C.

Research groups

Chemical Biology & Organic Synthesis

Publications

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Jump to: 2024 | 2023 | 2022 | 2021 | 2020 | 2019 | 2018 | 2017 | 2016 | 2014 | 2013 | 2011 | 2010 | 2009 | 2008

Number of items: 35.

2024

Masclef, J.-B., Acs, E. M. N., Koehnke, J. , Prunet, J. and Schmidt, B. V.K.J. (2024) PEGose block poly(lactic acid) nanoparticles for cargo delivery. Macromolecules, 57(13), pp. 6013-6023. (doi: 10.1021/acs.macromol.4c00528) (PMID:39005948) (PMCID:PMC11238580)

Masclef, J.-B., Prunet, J. and Schmidt, B. V.K.J. (2024) Synthesis of PEG-polycycloether block copolymers: poloxamer mimics containing a rigid helical block. Advanced Science, 11(22), 2310277. (doi: 10.1002/advs.202310277) (PMID:38520722)

2023

Audic, A. and Prunet, J. (2023) Synthesis of the CDF ring system of hexacyclinic acid. Synthesis, 55(15), pp. 2333-2342. (doi: 10.1055/a-2022-1809)

2022

Ojeda Porras, A. C., Aouzal, R., Wilson, C. and Prunet, J. (2022) Relay ring-closing metathesis strategies towards the synthesis of the ABC tricycle of Taxol. Tetrahedron, 106-07, 132630. (doi: 10.1016/j.tet.2022.132630)

2021

Brooks, S., Charlton, G., Letort, A., Prunet, J. and Bucher, G. (2021) Calculations on the ruthenium-catalyzed diene and dienyne ring-closing metathesis reactions in the synthesis of taxol derivatives. Journal of Organic Chemistry, 86(18), pp. 13056-13070. (doi: 10.1021/acs.joc.1c01879) (PMID:34449228)

Audic, A., Oriez, R. and Prunet, J. (2021) Dramatic influence of ester steric hindrance on the diastereoselectivity of a Michael addition towards the synthesis of the ABC tricycle of hexacyclinic acid. Tetrahedron, 79, 131843. (doi: 10.1016/j.tet.2020.131843)

2020

Garzón-Posse, F., Prunet, J. and Gamba-Sánchez, D. (2020) An alternative approach to the synthesis of the three fragments of Anachelin H. Organic and Biomolecular Chemistry, 18(14), pp. 2702-2715. (doi: 10.1039/D0OB00315H)

Altuna-Ruiz de Eguino, A., Cormack, P. A.G. and Prunet, J. (2020) Olefin cross metathesis as a versatile method for the facile functionalization of porous polymers. Organic Letters, 22(6), pp. 2481-2485. (doi: 10.1021/acs.orglett.0c00726) (PMID:32129631)

Wittmann, S., Tiniakos, A. F. and Prunet, J. (2020) Diastereoselective synthesis of trisubstituted olefins using a silicon-tether ring-closing metathesis strategy. Organic and Biomolecular Chemistry, pp. 2297-2306. (doi: 10.1039/C9OB02563D)

2019

Sanogo, Y., Othman, R. B., Dhambri, S., Selkti, M., Jeuken, A., Prunet, J. , Férézou, J.-P., Ardisson, J., Lannou, M.-I. and Sorin, G. (2019) Ti(II) and Rh(I) complexes as reagents toward a thapsigargin core. Journal of Organic Chemistry, 84(9), pp. 5821-5830. (doi: 10.1021/acs.joc.8b03249) (PMID:30964681)

2018

Becerra-Figueroa, L., Tiniakos, A. F., Prunet, J. and Gamba-Sánchez, D. A. (2018) Water-compatible synthesis of 2-trifluoromethyl-1,3-dioxanes. European Journal of Organic Chemistry, 48, pp. 6929-6932. (doi: 10.1002/ejoc.201801367)

Tiniakos, A. F., Wittmann, S., Audic, A. and Prunet, J. (2018) Novel synthesis of trisubstituted olefins for the preparation of the C16–C30 fragment of dolabelide C. Organic Letters, 21(3), pp. 589-592. (doi: 10.1021/acs.orglett.8b03552) (PMID:30589270)

Gamba-Sanchez, D. and Prunet, J. (2018) Synthesis of 1,3-diols by O-nucleophile additions to activated alkenes. Synthesis, 50(20), pp. 3997-4007. (doi: 10.1055/s-0037-1610248)

Alkattan, M., Prunet, J. and Shaver, M. (2018) Functionalizable stereocontrolled cyclopolyethers by ring-closing metathesis as natural polymer mimics. Angewandte Chemie (International Edition), 57(39), pp. 12835-12839. (doi: 10.1002/anie.201805113) (PMID:29873428) (PMCID:PMC6175094)

Jouanneau, M., Bonepally, K. R., Jeuken, A., Tap, A., Guillot, R., Ardisson, J., Férézou, J.-P. and Prunet, J. (2018) Diastereoselective synthesis of an advanced intermediate of thapsigargin and other 6,12-guaianolides using a RCEYM strategy. Organic Letters, 20(8), pp. 2176-2180. (doi: 10.1021/acs.orglett.8b00456) (PMID:29616815)

Morrison, S. D. , Liskamp, R. M.J. and Prunet, J. (2018) Tailoring polyethers for efficient post-polymerization functionalization by cross metathesis. Organic Letters, 20(8), pp. 2253-2256. (doi: 10.1021/acs.orglett.8b00595) (PMID:29600865)

Becerra-Figueroa, L., Movilla, S., Prunet, J. , Miscione, G. P. and Gamba-Sánchez, D. (2018) An intramolecular oxa-Michael reaction on α,β-unsaturated α-amino-δ-hydroxycarboxylic acid esters. Synthesis of functionalized 1,3-dioxanes. Organic and Biomolecular Chemistry, 16(8), pp. 1277-1286. (doi: 10.1039/c7ob03066e) (PMID:29384169)

2017

Sinclair, F., Alkattan, M., Prunet, J. and Shaver, M. P. (2017) Olefin cross metathesis and ring closing metathesis in polymer chemistry. Polymer Chemistry, 8(22), pp. 3385-3398. (doi: 10.1039/C7PY00340D)

Becerra-Figueroa, L., Brun, E., Mathieson, M., Farrugia, L. J., Wilson, C. , Prunet, J. and Gamba-Sánchez, D. (2017) Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction. Organic and Biomolecular Chemistry, 15(2), pp. 301-305. (doi: 10.1039/C6OB02333A) (PMID:27897299)

Adler, P., Fadel, A., Prunet, J. and Rabasso, N. (2017) From acyclic to cyclic α-amino vinylphosphonates by using ring-closing metathesis. Organic and Biomolecular Chemistry, 15(2), pp. 387-395. (doi: 10.1039/c6ob02548j) (PMID:27918059)

Prunet, J. (Ed.) (2017) Synthesis of Heterocycles by Metathesis Reactions. Series: Topics in heterocyclic chemistry. Springer: Switzerland. ISBN 9783319399393

2016

Fournier, L., Robert, C., Pourchet, S., Gonzalez, A., Williams, L., Prunet, J. and Thomas, C. M. (2016) Facile and efficient chemical functionalization of aliphatic polyesters by cross metathesis. Polymer Chemistry, 7(22), pp. 3700-3704. (doi: 10.1039/C6PY00664G)

Ma, C., Letort, A., Aouzal, R., Wilkes, A., Maiti, G., Farrugia, L. J., Ricard, L. and Prunet, J. (2016) Cascade metathesis reactions for the synthesis of taxane and isotaxane derivatives. Chemistry: A European Journal, 22(20), pp. 6891-6899. (doi: 10.1002/chem.201600592) (PMID:27062670) (PMCID:PMC4982030)

Letort, A., Long, D.-L. and Prunet, J. (2016) Study of cascade ring-closing metathesis reactions en route to an advanced intermediate of Taxol. Journal of Organic Chemistry, 81(24), pp. 12318-12331. (doi: 10.1021/acs.joc.6b02264) (PMID:27978745)

2014

Letort, A., Aouzal, R., Ma, C., Long, D.-L. and Prunet, J. (2014) Highly efficient synthesis of the tricyclic core of Taxol by cascade metathesis. Organic Letters, 16(12), pp. 3300-3303. (doi: 10.1021/ol501304j)

2013

Chevalley, A., Prunet, J. , Mauduit, M. and Ferezou, J.-P. (2013) Model studies for a ring-closing metathesis approach to the Bafilomycin macrolactone core from a 2,2-dimethoxy tetraenic ester precursor. European Journal of Organic Chemistry, 2013(36), pp. 8265-8278. (doi: 10.1002/ejoc.201300559)

Redon, S., Wierzbicki,, M. and Prunet, J. (2013) A new oxa-michael reaction and a gold-catalysed cyclisation en route to C-glycosides. Tetrahedron Letters, 54(16), pp. 2089-2092. (doi: 10.1016/j.tetlet.2013.02.022)

2011

Prunet, J. (2011) Progress in metathesis through natural product synthesis. European Journal of Organic Chemistry, 2011(20-21), pp. 3634-3647. (doi: 10.1002/ejoc.201100442)

Braun, M.G., Vincent, A., Boumediene, M. and Prunet, J. (2011) Highly demanding cross metathesis in the synthesis of the C16-C30 fragment of dolabelide C. Journal of Organic Chemistry, 76(12), pp. 4921-4929. (doi: 10.1021/jo200466t)

2010

Oriez, R. and Prunet, J. (2010) A two-step synthesis of allylic syn 1,3-diols via an intramolecular oxa-Michael reaction followed by a modified Julia olefination. Tetrahedron Letters, 51(2), pp. 256-258. (doi: 10.1016/j.tetlet.2009.10.139)

Gamba-Sanchez, D. and Prunet, J. (2010) Synthesis of modified methyl furanosides by intramolecular oxa-Michael reaction followed by Pummerer rearrangement. Journal of Organic Chemistry, 75(9), pp. 3129-3132. (doi: 10.1021/jo100241e)

2009

Gamba-Sanchez, D., Oriez, R. and Prunet, J. (2009) Regio- and diastereoselective addition of allylic thioethers to aldehydes. Tetrahedron Letters, 50(8), pp. 883-885. (doi: 10.1016/j.tetlet.2008.12.009)

Aouzal, R. and Prunet, J. (2009) Synthesis of functionalized Morita–Baylis–Hillman adducts by a conjugate addition–elimination sequence. Organic and Biomolecular Chemistry, 7(17), pp. 3594-3598. (doi: 10.1039/B907373F)

2008

Ma, C., Schlitz, S., Le Goff, X. and Prunet, J. (2008) Ring-closing metathesis in the synthesis of BC ring-systems of taxol. Chemistry: A European Journal, 14(24), pp. 7314-7323. (doi: 10.1002/chem.200800774)

Toueg, J. and Prunet, J. (2008) Dramatic solvent effect on the diastereoselectivity of Michael addition: study toward the synthesis of the ABC ring system of hexacyclinic acid. Organic Letters, 10(1), pp. 45-48. (doi: 10.1021/ol702566c)

This list was generated on Tue Jan 21 22:41:12 2025 GMT.

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