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Synthetic Methods for total Synthesis of Natural Products
English title
Synthetic Methods for total Synthesis of Natural Products
Applicant
Renaud Philippe
Number
119998
Funding scheme
Project funding (Div. I-III)
Research institution
Departement für Chemie, Biochemie und Pharmazie Universität Bern
Institution of higher education
University of Berne - BE
Main discipline
Organic Chemistry
Start/End
01.04.2008 - 31.03.2011
Approved amount
1'050'630.00
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Keywords (11)
organic synthesis; asymmetric synthesis; chiral relay radical reactions; non-toxic reagents; environmentally friendly processes; biologically active compounds; radical reactions; organometallic reagents; alkaloids; natural products; chiral catalysts
Lay Summary (English)
Lead
Lay summary
The total synthesis of natural products and analogues proved over the years to be the most reliable method for the discovery of new drugs. Due the structural complexity of many natural products, efficient synthetic methods are required to synthesize them. Our research program aims at finding methods and strategies that can be applied for efficient synthesis of different classes of products possessing an interesting biological profile. Development of processes involving radical chemistry, organometallic chemistry and enantioselective catalysis will be investigated. Our research focus on increasing the efficiency of target molecule synthesis by minimizing the number of synthetic steps, by opening new synthetic pathways, and by developing environmentally friendly reagents. The project is subdivided in six sub-chapters according to synthetic methods:
Boron reagents for radical chemistry. Our effort will be concentrated on the development of non-toxic and environmentally friendly reagents to perform efficient radical reactions. Organoboranes will be used as radical precursors and as reagents to replace toxic tin derivative for a wide range of radical reactions.
Activation of water and alcohols by boron derivatives. Replacing toxic reagent such as metal hydrides (in particular tin hydride) by water and alcohols for the reduction of radicals is a particularly promising research field to expend the utility of radical reactions.
Radical translocation-cyclization processes. Selective activation of an unreactive position of an organic molecule without using any transition metal can be accomplished via radical 1,5-hydrogen transfer. Extension of this chemistry to cascade reactions will shorten dramatically the length of some natural product syntheses.
Radical Azidation. The formation of carbon-nitrogen bonds under very mild reaction conditions represents a very useful tool for the total synthesis of alkaloids. Efficient reagents to achieve such a transformation are under development.
Annulation reactions via carbometallation of non activated alkynes. This project is directed towards the preparation of moderately complex chiral building blocks for the synthesis of biologically relevant products. A novel annulation procedure will be developed that should afford 5-membered rings via a domino reaction.
Preparation of N-heterocyclic compounds. In this part, an efficient functionalization of lactams will be used to prepare advanced building block for alkaloid synthesis. Desymmetrization of spirocyclic lactams will be examined in order to prepare to optically pure alkaloids. Application of this chemistry for the preparation of Cephalotaxus alkaloids, a class of very potent anticancer agents, will be developed.
Direct link to Lay Summary
Last update: 21.02.2013
Responsible applicant and co-applicants
Name
Institute
Renaud Philippe
Departement für Chemie, Biochemie und Pharmazie Universität Bern
Employees
Name
Institute
Bürki Cédric
Departement für Chemie, Biochemie und Pharmazie Universität Bern
Lapointe Guillaume
Division of Chemistry and Chemical Engineering California Institute of Technology
Villa Giorgio
The Scripps Research Institute
Lamarque Christophe
Princeton University Dept. of Chemistry
Weidner Karin
Department of Chemistry The Scripps Research Institute
Agosti Alessandro
Department of Chemistry Massachusetts Institute of Technology
Garnier Jean
Brucelle François
Group Prof. M. Movassaghi Department of Chemistry Massachusetts Institute of Technology (MIT)
Associated projects
Number
Title
Start
Funding scheme
112250
Synthetic Methods for total Synthesis of Natural Products
01.04.2006
Project funding (Div. I-III)
135087
Synthetic Methods for total Synthesis of Natural Products
01.04.2011
Project funding (Div. I-III)
128724
Purchase of a single crystal X-ray diffractometer for high resolution and accurate studies on molecular crystals
01.12.2009
R'EQUIP
135087
Synthetic Methods for total Synthesis of Natural Products
01.04.2011
Project funding (Div. I-III)
-