Group
II.
Stereocontrolled Synthesis of Antibiotics and Related Microbial Products
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Head of the group Prof. Marek Chmielewski e-mail: <chmiel@icho.edu.pl>
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Ph.D.,
1972, Institute of Organic Chemistry PAS. |
Staff:
Magdalena Dziedzic Ph.D. student; Bartłomiej Furman, D.Sc.; Barbara Grzeszczyk Ph.D.; Anna Jałmużna Ph.D. student; Margarita Jurczak, Ph.D.; Iwona Kazimierczak technician; Wioletta Kośnik Ph.D. student; Grzegorz Lipner Ph.D. student; Marek Masnyk Ph.D.; Konrad Paśniczek Ph.D.; Sebastian Stecko Ph.D. student; Bartosz Zambroń Ph.D. student; Sylwester Żochowski technician .
Research activity
The major research interest involves stereocontrolled synthesis of oxygen analogs of penicillins and cephalosporins. Particular attention is directed to stereoselectivity of the [2+2]cycloaddition of chlorosulfonyl isocyanate to chiral vinyl ethers and the aplication of readily available 4-vinyloxy-azetidin-2-one as b-lactam building block. Both methodologies are adapted for a solid-phase synthesis. Current interest includes also synthesis and transformations of unsaturated sugar 1,4- and 1,5-lactones. Special attention is concentrated on the conjugate addition-rearrangement of hydroxylamines and hydrazines, as well as, 1,3-dipolar cycloaddition of chiral nitrones to these lactones with the intention to synthesize aminodeoxy- and iminosugars. Other project presently conducted involve: synthesis of anomeric hydroperoxides with the intention to use them as chiral epoxidation reagents (Prof. Marek Chmielewski).
Stereocontrolled synthesis of indolizidines and quinolizidines via cyclizations involving allyl, vinyl and propargyl silanes and stannanes, or vinyl iodides to dihydropyridones. The other project involves intramolecular reactions of oxocarbenium ions (Prins-type cyclization) with intention to the synthesis of highly substituted oxepanes. (Bartłomiej Furman D.Sc.)
Selected scientific publications
1 C. Bełżecki, R. Urbański, Z. Urbańczyk-Lipkowska, M. Chmielewski: Tetrahedron, 53, 14153 (1997), “Synthesis of 1-oxacephams from D-arabinal and L-rhamnal”.
2. J. Rabiczko, M. Chmielewski: J. Org. Chem., 64, 1347 (1999), “A new route to bicyclic pyrazolidinones and hydroxypyrrolidines from α,β-unsaturated sugar δ-lactones”.
3. B. Furman, R. Thürmer, Z. Kałuża, R. Łysek, W. Voelter, M. Chmielewski, Angew. Chem., Int. Ed. Engl., 1121 (1999), “Stereoselective solid-phase synthesis of β-lactams, A novel cyclization/cleavage step towards 1-oxacephams”.
4. R. Łysek, B. Furman, Z. Kałuża, J. Frelek, K. Suwińska, Z. Urbańczyk-Lipkowska, M. Chmielewski: Tetrahedron: Asymmetry, 11, 3131 (2000), “[2+2]Cycloaddition of chlorosulfonyl isocyanate to allenylsugar ethers”.
5. R. Łysek, K. Borsuk, M. Chmielewski, Z. Kałuża, Z. Urbańczyk-Lipkowska, A. Klimek, J. Frelek: J. Org. Chem, 67, 1472 (2002), “5-Dethia-5-oxacephams: Towards correlation of absolute configuration and chiroptical properties”.
6. J. Rabiczko, Z. Urbańczyk-Lipkowska, M. Chmielewski: Tetrahedron, 58, 1433 (2002), “Syntheses of pyrrolizidines and indolizidines from α,β-unsaturated sugar δ-lactones via Dieckmann condensation”.
7. K. Borsuk, A. Kazimierski, J. Solecka, Z. Urbańczyk-Lipkowska, M. Chmielewski: Carbohydr. Res., 337, 2005 (2002), „Stereocontrolled formation of oxacephams from carbohydrates”.
8. R. Łysek, K. Borsuk, B. Furman, Z. Kałuża, A. Kazimierski, M. Chmielewski: Curr. Med. Chem.,11, 1813 (2004), “Strategies for the stereocontrolled formation of oxygen analogs of penicillins and cephalosporins”.
9. B. Furman, K. Borsuk, Z. Kałuża, R. Łysek, M. Chmielewski: Curr. Org. Chem., 8, 463 (2004), “Stereochemistry of [2+2]cycloaddition of chlorosulfonyl isocyanate to olefins”.
10. Tong Thanh Danh, K. Borsuk, J. Solecka, M. Chmielewski, Tetrahedron, 62, 10928 (2006) “An entry to 7- amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-L-erythritol”.
11. K. Paśniczek, D. Socha, M. Jurczak, J. Solecka, M. Chmielewski, Can. J. Chem., 84, 534 (2006) „Synthesis of 8-Homocastanospermine”.
12. S. Stecko, K. Paśniczek, M. Jurczak, Z. Urbańczyk-Lipkowska M. Chmielewski, Tetrahedron: Asymmetry, 17, 68 (2006), „Double asymmetricinduction in 1,3-dipolar cycloaddition of five-membered cyclic nitrones to 2-(5H)-furanones”.
13. W. Kośnik, A. Stachulski M. Chmielewski Tetrahedron: Asymmetry, 16, 1975 (2005), „New stable anomeric hydroperoxides derived from 2-deoxy-sugars; Enantioselective epoxidation of 2-methyl-1,4-naphtoquinone”.
14. M. Chmielewski, R. Łysek, B. Grzeszczyk, B. Furman: Eur. J. Org. Chem., 4177 (2004), “[2+2]Cycloaddition of chlorosulfonyl isocyanate to (Z)-propenyl ethers bound to polystyrene resins via alkylsulfonyl linkers”.
15. K. Paśniczek, D. Socha, M. Jurczak, J. Frelek, A. Suszczyńska, Z. Urbańczyk-Lipkowska, M. Chmielewski: J. Carbohydr. Chem., 22, 613 (2003) “Double asymmetric Induction in 1,3-dipolar cycloaddition of nitrones to 2,3-unsaturated sugar 1,5-lactones”.
16. B. Furman, M. Dziedzic: Terahedron Lett., 44, 6629 (2003) “Tetrabutylammonium triphenyldifluorosilicate (TBAT) initiated intramolecular addition of allylsilanes to 2,3-dihydro-4-pyridones. A novel route for the stereoselective constructionof indolizidine systems”.
17. R. Łysek, E. Woźny, Tong Thanh Danh, M. Chmielewski: Tetrahedron Lett., 44, 7541 (2003), “Formation of (E) 1-alkoxy-1,3-butadienes from corresponding propargyl ethers; vicarious nucleophilic substitution in alkoxyallenes”.
18. B. Furman, K. Borsuk, Z. Kałuża, R. Łysek, M. Chmielewski, Curr. Org. Chem., 8, 463 (2004), “Stereochemistry of [2+2]cycloaddition of chlorosulfonyl isocyanate to olefins”.
19. Furman, B.; Dziedzic, M. Tetrahedron Lett., 44, 8249 (2003), „An efficient route to 4-(substituted benzyl)piperidines” .
20. Dziedzic, M.; Małecka, M.; Furman, B., Org. Lett., 7, 1725 (2005), „Rhodium-catalyzed intramolecular conjugate addition of vinylstannanes to 2,3-dihydro-4-pyridones. An efficient route to stereoselective construction of indolizidines” .
21. Furman, B.; Dziedzic, M.; Lipner, G.; Illangua, J. M., Tetrahedron, 61, 8641 (2005), ”The fluoride ion-induced intramolecular conjugate addition of propargylsilanes to dihydropyridones. A novel method for the stereoselective construction of azabicyclic ring systems” .
22. Dziedzic, M.; Lipner, G.; Furman, B., Tetrahedron Lett., 46, 6861 (2005), ”An efficient approach to the synthesis of 3-vinylidene tetrahydropyrans via prins-type cyclization” .
23. R. Łysek, K. Borsuk, B. Furman, Z. Kałuża, A. Kazimierski, M. Chmielewski, Curr. Med. Chem., 11, 1813, (2004), “Strategies for the stereocontrolled formation of oxygen analogs of penicillins and cephalosporins”.
24. J. Młynarski, M. Mitura, Tetrahedron Lett., 45, 7549 (2004), “The first example of a catalytic asymmetric Aldol-Tishchenko reaction of aldehydes and aliphatic ketones” .
25. J. Młynarski,. Eur. J. Org. Chem., 4779 (2006) “Direct asymmetric Aldol-Tishchenko reaction microreview".
26. J. Młynarski, B Rakiel. M. Stodulski, A. Suszczyńska, J. Frelek, Chem. Eur. J., 12, 8158 (2006), “The chiral ytterbium complexes-catalyzed direct asymmetric Aldol-Tishchenko reaction. Synthesis of anti-1,3-diols”.
27. Jankowska, J.; Mlynarski, J, J. Org. Chem., 71, 1317 (2006), “Zn(pybox)-complex catalyzed asymmetric aqueous Mukaiyama-Aldol reactions”.
