Group II. 
Stereocontrolled Synthesis of Antibiotics and Related Microbial Products

Bartłomiej Furman D.Sc.

Research activity:

The focus of our interests is the development of new synthetic reactions, and in the application of those transformations to the synthesis of complex molecular structures. The reactions that particularly interest us are those that afford products with control of stereochemistry.

Construction of azabicyclic alkaloids. We have recently discovered highly stereoselective approach to the construction of indolizidines, quinolizidines and some higher homologues, based on intramolecular conjugate addition of allylsilanes, propargylsilanes, vinylstannanes or vinyl iodides to dihydropyridones. The methodology developed has been applied to the synthesis of (±) Lasubine I.

Intramolecular reactions of oxocarbenium ions (Prins-type cyclization). We have been interested in employing propargylsilanes and vinylstannanes to construct tetrahydropyrans with high stereoselectivity. In addition, we have applied these reactions to the synthesis of highly substituted oxepanes.

 Selected publications:

1.    Furman, B.; Dziedzic M. „Tetrabutylammonium Triphenyldifluorosilicate (TBAT) Initiated Intramolecular Addition of Allylsilanes to 2,3-Dihydro-4-pyridones. A Novel Route for the Stereoselective Construction of Indolizidine Systems” Tetrahedron Lett., 2003, 44, 6629-6632.

2.    Furman, B.; Dziedzic, M. „An Efficient Route to 4-(Substituted benzyl)piperidines” Tetrahedron Lett., 2003, 44, 8249-8252

3.    Dziedzic, M.; Małecka, M.; Furman, B. „Rhodium-Catalyzed Intramolecular Conjugate Addition of Vinylstannanes to 2,3-Dihydro-4-pyridones. An Efficient Route to Stereoselective Construction of Indolizidines” Org. Lett. 2005, 7, 1725-1727.

4.   Furman, B.; Dziedzic, M.; Lipner, G.; Illangua, J. M. ”The Fluoride Ion-Induced Intramolecular Conjugate Addition of Propargylsilanes to Dihydropyridones. A Novel Method for the Stereoselective Construction of Azabicyclic Ring Systems” Tetrahedron 2005, 61, 8641-8647.

5.   Dziedzic, M.; Lipner, G.; Furman, B. ”An Efficient Approach to the Synthesis of 3-Vinylidene Tetrahydropyrans via Prins-type Cyclization” Tetrahedron Lett., 2005, 46, 6861-6863.

6.   Furman, B.; Frelek, J.; Dziedzic, M.; Kamińska, A. “Asymmetric Synthesis of Multi-substituted Indolizidines by Intramolecular Addition of Allylsilane to Chiral 2,3-Dihydro-4-pyridones” Pol. J. Chem., 2005, 79, 1919-1928.

7.   Pleuss, N.; Zech, G.; Furman, B.; Kunz, H. In The Organic Chemistry of Sugars; Levy, D.E., Fugedi, P. Eds.; CRC Press 2006, pp. 427-481.