Dr Joelle Prunet

  • Senior Lecturer (Chemistry)

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

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.

Selected publications

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)

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)


All publications

List by: Type | Date

Jump to: 2017 | 2016 | 2014 | 2013 | 2011 | 2010 | 2009 | 2008
Number of items: 18.

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 Wed Sep 20 14:11:15 2017 BST.
Number of items: 18.

Articles

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)

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)

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)

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)

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)

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)

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)

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)

Edited Books

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

This list was generated on Wed Sep 20 14:11:15 2017 BST.