Philip Kocienski

Research section: Organic Chemistry

KEYWORDS Organometallic chemistry Synthesis Natural products Antibiotics Vitamins Antifungal agents Antitumour agents, immunosuppressants Antiviral agents Antiinflammatory agents Enzyme inhibitors

RESEARCH INTERESTS

Our research concerns the development of new synthetic methods and their application to the synthesis of biologically active natural products. A conspciuous example is the sulfone-based olefination (the Julia–Kocienski reaction) which we developed for the synthesis of herboxidiene and rapamycin. It is now widely used in fragment linkage reactions in complex natural prodyuct synthesis. Our interests also embrace various aspects of organometallic chemistry such as the use of planar chiral cationic π-allylmetal complexes for the stereospecific appendage of chains to rings and the stereoselective synthesis of trisubstituted alkenes via copper(I)-mediated1,2-metallate rearrangements which features in our syntheses of D-erythro-sphingosine and manoalide.

SELECTED PUBLICATIONS

A Synthesis of Manoalide via a Copper(I)-Mediated 1,2-Metallate Rearrangement. Pommier, A.; Stepanenko, V.; Jarowicki, K.; Kocienski, P. J. J. Org. Chem. 2003, 68, 4008-4013

The Nucleophilic Addition of α-Metallated 1,3-Dioxane to Planar Chiral Cationic η³-Allylmolybdenum Complexes. Synthesis of (2E,5S,6R,7E)-6-Methyl-8-phenylocta-2,7-dienoic Acid Methyl Ester, a Key Component of the Cryptophycins. Cooksey, J.; Gunn, A.; Kocienski, P. J.; Kuhl, A.; Uppal, S.; Christopher, J. A.; Bell, R. Org. Biol. Chem. 2004, 2, 1719-1731.

Synthesis of (S)-(–)-N-Acetylcolchinol Using Intramolecular Biaryl Oxidative Coupling. Besong, G.; Jarowicki, K.; Kocienski, P. J.; Sliwinski, E.; Boyle, F. T. Org. Biomol. Chem. 2006, 4, 2193-2207

Synthesis of the C1-C16 Fragment of Ionomycin Using a Neutral (η³-Allyl)iron Complex. Cooksey, J. P.; Kocienski, P. J.; Li, Y.; Schunk, S.; Snaddon, T. N. Org. Biomol. Chem. 2006, 4, 3325-3336