Group
XVIII.
Synthesis of Natural Products and Relevant Synthesis MetHodology
|
Head of the group Prof. Jerzy Wicha e-mail:<wicha@icho.edu.pl> |
Ph.D., 1964, Department of Chemistry, University. of Warsaw. Habilitation, 1970, Department of Chemistry, University of Warsaw. Post-doc., Worcester Foundation for Experimental Biology, Shrewsbury, Massachusetts, USA, 1964-1966 and Dyson Perrins Laboratory, Oxford University, England, 1966/1967. Senior Visiting Scientist, Department of Chemistry, University of Chicago, USA, 1978/79. Visiting Professor, Department of Biochemistry, University of Wisconsin at Madison, USA. 1990/1991. Visiting Professor, University of Cape Town, Republic of South Africa, 1996. Award for Young Scientists, Polish Chemical Society, 1968 Award of the Scientific Secretary of PAS, 1990 Heyrovsky Gold Medal of the Czechoslovak Academy of Sciences 1991 St. Kostanecki Medal of the Polish Chemical Society 1996. |
Staff:
Ph.D.Paweł Jankowski,Ph.D.Karol Michalak,Ph.D., Andrzej Zarecki, Ph. D. students: Krzysztof Pleśniak, Michał Michalak, Paweł Szymanek, Paweł Chocherek
Research activity
One of our long-term interests has been linked with development of methods for the synthesis of natural products, mainly of polycyclic nature, as vitamin D metabolites, cardenolides and other steroids, but also certain pheromones, prostanoids, small-ring compounds, building blocks for macrocyclic antibiotics. Our studies embrace total synthesis as well as transformations of abundant natural precursors. In total synthesis we seek for stereoselective methods of general value, particularly for tandem reactions allowing reducing number of synthetic operations. An emphasis is made on application of catalytic enantioselective reactions, particularly the conjugate addition in the presence of optically active binaphthyl derivatives or certain aminoacids. In partial synthesis we focus on natural products with unusual structural features, such as cyclopropene or methylenecyclopropane rings. Target compounds include new analogues of vitamin D with potential therapeutic value.
Within synthetic methodology, we are interested in the chemistry of organosilicon compounds including those with a stereogenic silicon atom. Other interests in this area embrace sulfone - based alkenylation and cross - coupling reactions.
Selected scientific publications:
1.
A. Kurek-Tyrlik, K. Minksztym and J. Wicha,
J. Am. Chem.
Soc.,
117, 1849 (1995), “Syntheis of (23R)- and (23S)- 23H
Isocalysterols. The First Synthesis of a Representative of Marine Sterols,
with Cyclopropene Moiety in the Side Chain”.
2.
P. Grzywacz, S. Marczak and J. Wicha, J. Org. Chem.,
62, 5293 (1997), “Synthesis of Vitamin D3 Hydrinadane
Rings - Side Chain Building Block, Involving Tandem Conjugate Addition and
Alkylation Reaction”.
3.
B. Achmatowicz, P. Jankowski, J. Wicha and A. Zarecki, J.
Orgnomet. Chem.,
558, 227 (1998), “Migration of Aryl Groups from Silicon to Carbon
in á,â-epoxysilanes. A New Model for a Hypervalent Silicon Study”.
4.
P. Jankowski, S. Marczak and J. Wicha, Tetrahedron 54,
12071 (Report 467). (1998), “Methods for Construction of trans-Hydrindane
Rings and their Origins in Steroid Chemistry. Vitamin D Total Synthesis”.
5.
B. Achmatowicz, E.
Gorobets, S.Marczak, A. Przezdziecka, A.
Steinmeyer, J. Wicha*, U. Zügel, Tetrahedron Lett. 2001,
42, 2891-2895 “The first synthesis and biological testing of the
enantiomer of 1α,25-dihydroxyvitamin D3”
6.
Alicja
Kurek-Tyrlik, Stanisław Marczak, Karol Michalak, Jerzy Wicha* and Andrzej
Zarecki, J. Org. Chem.
2001, 66, 6994-7001
„Reaction of arylsulfonylhydrazones of aldehydes with a-magnesio
sulfones. A novel olefin synthesis”.
7.
Paweł Jankowski,
Krzysztof Pleśniak and Jerzy Wicha, Org. Lett.,
2003, 5, 2789-2792
„An
Efficient Synthesis of Vinylsilanes from Acylsilanes and Alkyl 1-Phenyl-1H-tetrazol-5-yl
Sulfones. Brook vs. Smiles Rearrangement”.
8.
Evgueni Gorobets,
Viatcheslav Stepanenko, Jerzy Wicha, Eur J. Org. Chem.
2004, 783-799 “Enantioselective
Total Synthesis of Vitamin D trans-Hydrindane Rings – Side Chain
Building Block. Asymmetric
Induction in Acid-catalyzed Conjugate Addition Reaction”.
9.
Jerzy Wicha,
Andrzej Zarecki, J. Org. Chem.
2004, in the press „Olefination
of a-Hydroxy-
or a-Aminoaldehyde
Derivatives via Reaction of their Arylsulfonylhydrazones with Sulfonyl
Anions”.
10. Karol Michalak, Michał Michalak, Jerzy Wicha, Org. Lett. 2004, submitted, „Synthesis of Cyclooctapentanes or Cyclopentaannulenes from Dienes Derived from 2-Methylcyclopent-2-en-1-one. Remote Steric and Substituent Effects in the Ring Closing Metathesis Reaction”.
