PAVOL JAKUBEC

BIOGRAPHY

“Akýkoľvek výskum je v dnešnej dobe prácou veľkého tímu ľudí. Každý jednotlivec prispieva len maličkou časťou k celkovému výsledku.”

Pavol studied at the Slovak University of Technology in Bratislava, Slovakia where he received his Masters degree in 2001 and his DPhil in 2005 for work supervised by Prof Dušan Berkeš. 

He spent his first post-doctoral stays with Professor Darren J. Dixon at The University of Manchester (2006-2008) and at the University of Oxford (2008-20014) working on method and catalyst developments and especially on total synthesis of complex natural products of the manzamine class. 

In 2014 he moved for another post-doctoral stay working for Prof. Andrew G. Myers at the Harvard University on macrolide antibiotics (2014-2016). 

In 2016 he moved to his current post at the Slovak University of Technology in Bratislava where he is research assistant. His research program, part of the investigation in the group of Prof. Dušan Berkeš, is focused on crystallization-induced asymmetric transformation and its application in synthesis of biologically active substances.

Auchem s.r.o. is a contract organization specializing in synthesisof fine organic chemicals, various important synthetic intermediates, and medicinally relevant substances. It was founded by Ferdinand Straka and Pavol Jakubec (scientific director) in 2016 and began producing the same year.

EXTRAORDINARY EXPERIENCES

– post-doctoral stays with Professor Darren J. Dixon at The University of Manchester (2006-2008) and at the University of Oxford (2008-20014) 


– another post-doctoral stay working for Prof. Andrew G. Myers at the Harvard University on macrolide antibiotics (2014-2016)

PRIZES AND AWARDS

1. “Accelerator” post-doctoral fellowship (Harvard University, 
2014-2016)
2. 2nd Syngenta Postdoc Symposium, Oxford, March 20, 2014 – one of three price-awarded presentation
3. EPSRC post-doctoral fellowship (Oxford University, 2008-2014)
4. Challenges in Organic & Bioorganic Chemistry: 14th Tetrahedron 
Symposium, Vienna, Austria, June 25-28 2013 – one of the four selected presentations from all contributing abstracts.
5. Marie-Curie IEF post-doctoral fellowship for career development 
(MEIF-CT2007-039987, The University of Manchester, 2006-2008)
6. Master of Science (M.Sc.) – Award for excellence – graduated with 
honors 2001
7. Student Research and Professional Activities (“ŠVOČ”) at FCHPT STU Slovakia – winner of the “Organic Chemistry” section in 2000.

 
 
 

Publications

  1. Marčeková, M.; Gerža, P.; Šoral, M.; Moncol, J.; Berkeš, D.; Kolarovič, A.; Jakubec, P.; Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction Lett. 2019, 21, 4580-4584.
  2. Ferko, B.; Zeman, M.; Formica, M.; Veselý, S.; Doháňošová, J.; Moncol, J.; Olejníková, P.; Berkeš, D.; Jakubec, P; Dixon, D. J.; Caletková, O.; Total Synthesis of Berkeleylactone A Org. Chem. 2019, 84, 7159-7165
  3. Ďuriš, A.; Berkeš, D.; Jakubec, P.; Stereodivergent Synthesis of Cyclic γ-Aminobutyric Acid-GABA Analogues, Tetrahedron Lett. 2019, 60, 480-484.
  4. Sivák, I.; Toběrný, M.; Kyselicová, A.; Caletková, O.; Berkeš, D.; Jakubec, P.; Kolarovič, A.; Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration; Org. Chem. 2018, 83, 15541-15548.
  5. Farley, A. J. M.; Jakubec, P.; Goldys, A. M.; Dixon, D. J.; Bifunctional iminophosphorane superbases: Potent organocatalysts for enantio-and diastereoselective Michael addition reactions; Tetrahedron 2018.
  6. Shi, H.; Michaelides, I. N.; Darses, B.; Jakubec, P.; Nguyen, Q. N. N.; Paton, R. S.; Dixon, D. J.; Total synthesis of (−)-himalensine A; Am. Chem. Soc. 2017, 139, 17755-17758.
  7. Seiple, I. B.; Zhang, Z.; Jakubec, P.; Langlois-Mercier, A.; Wright, P. M.; Hog, D. T.; Yabu, K.; Allu, S. R.; Fukuzaki, T.; Carlsen, P. N.; Kitamura, Y.; Zhou, X., Condakes, M. L.; Szczypiński, F. T.; Green, W. D.; Myers, A. G.; A platform for the discovery of new macrolide antibiotics; Nature 2016, 533,
  8. Jakubec, P.; Farley, A. J. M.; Dixon, D. J.; Towards the total synthesis of keramaphidin B; Beilstein J. Org. Chem. 2016, 12, 1096–1100
  9. Franchino, A.; Jakubec, P.; Dixon, D. J.; Synthesis of (–)-chloramphenicol; Biomol. Chem. 2016, 14, 93-96 (Highlighted in: Synfacts 2016, 12, 219)
  10. Jakubec, P.; Muratore, M. E.; Aillaud, I.; Thompson, Amber L.; Dixon, Darren J.; Design, synthesis and applications of new families of chiral sulfonic acids; Tetrahedron: Asymmetry 2015, 26, 251-261.
  11. Gregory, A. W.; Chambers, A.; Hawkins, A.; Jakubec, P.; Dixon, D. J.; Iridium-Catalyzed Reductive Nitro-Mannich Cyclization; Eur. J. 2015, 21, 111-114.
  12. Kang, B.; Jakubec, P.; Dixon, D. J.; Strategies towards the synthesis of calyciphylline A type Daphniphyllum alkaloids; Prod. Rep. 2014, 31, 550-562.
  13. Gregory, A. W., Jakubec, P.; Turner, P.; Dixon, D. J.; Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-sulfonyliminium Cyclization Cascade Org. Lett. 2013, 15, 4330-4333.
  14. Wang, C.; Yu, M.; Kyle, A. F.; Jakubec, P.; Dixon, D. J.; Schrock, R. R.; Hoveyda, A. H.; Efficient and Selective Formation of Macrocyclic Disubstituted Z Alkenes by Ring-Closing Metathesis (RCM) Reactions Catalyzed by Mo- or W-Based Monoaryloxide Pyrrolide (MAP) Complexes: Applications to Total Syntheses of Epilachnene, Yuzu Lactone, Ambrettolide, Epothilone C, and Nakadomarin A; Eur. J. 2013, 19, 2726-2740 (VIP paper).
  15. Hawkins, A.; Jakubec, P.; Ironmonger, A.; Dixon, D. J.; An expedient stereoselective route to the ACE tricyclic core of manzamine A via a palladium-catalysed arylative allene spirocyclisation cascade; Tetrahedron Lett. 2013, 54, 365-369.
  16. Jakubec, P.; Hawkins, A.; Felzmann, W.; Dixon, D. J.; Total Synthesis of Manzamine A and Related Alkaloids; J. Am. Chem. Soc. 2012, 134, 17482-17485 (Highlighted in: Synfacts 2013, 9, 17; Organic chemistry portal – total synthesis series May 6 2013. The most read paper in J. Am. Chem. Soc. in November 2012. Included among top 20 most read papers in J. Am. Chem. Soc. 2012/13).
  17. Jakubec, P.; Cockfield, D. M.; Helliwell, M.; Raferty, J.; Dixon, D. J.; Stereoselective, nitro-Mannich/lactamisation cascades for the direct synthesis of heavily decorated 5-nitropiperidin-2-ones and related heterocycles; Beilstein J. Org. Chem. 2012, 8, 567-578.
  18. Yu, M.; Wang, C.; Kyle, A. F.; Jakubec, P.; Dixon, D. J.; Schrock, R. R.; Hoveyda, A. H.; Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis; Nature 2011, 479, 88-92. (Highlighted in: C&EN 2011, 89, 11).
  19. Jakubec, P.; Kyle, A. F.; Calleja, J.; Dixon, D. J.; Total synthesis of (–)-nakadomarin A: alkyne ring-closing metathesis; Tetrahedron Lett. 2011,  52, 6094-6097. (Front cover of Tetrahedron Lett. 2011, 52, issue 46).
  20. Jakubec, P.; Hynes, P. S.; Cockfield, D. M.; Cleator, E.; Dixon, D. J.; Enantio- and diastereoselective Michael additions of C-succinimidyl esters to nitro olefins using cinchonine-derived bifunctional organocatalysts; Tetrahedron: Asymmetry 2011, 22, 1147-1155.
  21. Kyle, A.; Jakubec, P.; Cockfield, D. M.; Cleator, E.; Skidmore, J.; Dixon, D. J.; Total synthesis of (–)-nakadomarin A; Chem. Commun. 2011, 47, 10037-10039.
  22. Jakubec, P.; Berkeš, D.; Crystallisation-induced asymmetric transformation (CIAT) for the synthesis of dipeptides containing homophenylalanine; Tetrahedron: Asymmetry 2010, 21, 2807-2815.
  23. Jakubec, P.; Petráš, P.; Duriš, A.; Berkeš, D.; The first example of a crystallization-induced asymmetric transformation (CIAT) in the Mannich reaction; Tetrahedron: Asymmetry 2010, 21, 69-74.
  24. Jakubec, P.; Cockfield, D. M.; Dixon, D. J.; Total Synthesis of (–)-Nakadomarin A; J. Am. Chem. Soc. 2009, 131, 16632-16633 (Highlighted in: Chemistry world 2009, Angew. Chem. Int. Ed. 2010, 49, 2830-2832; Synfacts 2010, 3, 272-272; Organic chemistry portal – total synthesis series May 3 2010. Included among top 20 most read papers in J. Am. Chem. Soc. 2009).
  25. Jakubec, P.; Halliwel, M.; Dixon, D. J.; Cyclic imine nitro-Mannich/lactamization cascades: A direct stereoselective synthesis of multicyclic piperidinone derivatives; Org. Lett. 2008, 10, 4267-4270.
  26. Solčan, T.; Jakubec, P.; Prónayová, N.; Milata, V.; Behaviour of enaminomalonates and enamidomalonates under various reductive conditions: A novel synthetic approach to N-acyl-N-aryl β-amino acids; Tetrahedron Lett. 2008, 49, 2631-2633.
  27. Berkeš, D.; Jakubec, P.; Winklerová, D.; Považanec, F.; Daich, A.; CIAT with simultaneous epimerisation at two stereocenters. Synthesis of substituted β-methyl-α-homophenylalanines; Org. Biomol. Chem. 2007, 5, 121-124.
  28. Jakubec, P.; Berkeš, D.; Kolarovič, A.; Považanec, F.; Asymmetric synthesis of aliphatic α-amino and γ-hydroxy α-amino acids and introduction of a template for crystallisation-induced asymmetric transformation; Synthesis 2006, 23, 4032-4040.
  29. Jakubec, P.; Berkeš, D.; Šiška, R.; Gardianová, M.; Považanec, F.; Crystallisation induced asymmetric transformation (CIAT) in the synthesis of furoylalanines and furylcarbinols; Tetrahedron: Asymmetry 2006, 17, 1629-1637.
  30. Rossen, K.; Jakubec P.; Kiesel M.; Janik M.; A new synthesis of b-aminoacids by use of ketene diethylacetal as enolate equivalent; Tetrahedron Lett. 2005, 46, 1819-1821.
  31. Jakubec, P., Berkeš, D.; Považanec, F.; Crystallisation-induced asymmetric transformation. Application to conjugate addition of benzylamine to amides of benzoylacrylic acid; Tetrahedron Lett. 2004 45, 4755-4758.

Patents

  1. Most, D.; Jakubec, P.; Rossen, K.; Process for the production of a-alkoxy/hydroxy-b-(p-hydroxyphenyl)propionic acid derivatives; 2005 WO 200502096 A3.
  2. Rossen, K.; Jakubec, P.; Process for the preparation of β-aminocarboxylic acids; 2005 WO 2005095325.