Synthese von 13C-markierten Intermediaten in der Biosynthese der Paraherquamide- und Asperparaline-Alkaloide

• Applicant: Dr. Konrad Miroslaw Sommer
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2003 to 2005
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 5403521

The biosynthesis of complex, biologically active natural products are pursued with the ultimate objectives of probing, understanding and manipulating the genetic machinery of complex, secondary metabolite construction in bacteria, fungi, and plants. In this area, the research group of Prof. R. M. Williams has targeted biosynthetic pathway of paraherquamide family of alkaloides that have unusual intrigue and potential commercial importance. Extensive use of natural product total synthesis and radioisotope synthesis of biosynthetic intermediates and biological methods are being employed to map and probe secondary metabolic pathways in detail. As a part of a program directed at elucidating the biosynthesis of paraherquamide A and asperparaline A, the goal of this project is it to provide with the help of modern synthetic chemistry a library of 13C-labeled biosynthetic intermediates of those anthelmintic efective alkaloides, to perform feeding experiments and to elucidate so the biosynthesis of the core bicyclo[2.2.2] ring system of the paraherquamide A, and the origin of the spiro-succinimide ring system of asperparaline A. These studies are to be carried out in convention with the group of Professor R. M. Williams, where the underlying total synthesis were completed. The planned, high-convergent synthesis strategy proceeds from comercially accessible starting materials and concentrates on the apllication of modified methodology originally developed for the stereocontrolled total synthesis of (+)-paraherquamide B.

• DFG Programme: Research Fellowships
• International Connection: USA
• Cooperation Partner: Professor Dr. Robert M. Williams