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New Organocatalytic Malononitrile Michael Addition Methodology for the Enantioselective Synthesis of Calyciphylline K

Objective

Calyciphylline K is a Daphnezomine L-type natural product with promising anticancer activity. We propose to complete the total synthesis of Calyciphylline K and several closely-related Daphnezomine L alkaloids by developing a novel asymmetric organocatalytic Malononitrile Michael Addition methodology to facilitate their preparation in a short sequence of around 12 synthetic steps. The anticancer activity of Calyciphylline K and other analogues prepared during this study will then be evaluated using Alamar Blue cell viability assays, followed by further study in collaboration with the Structural Genomics Consortium (SGC), where high-throughput kinase screening assays are available to further understand their pharmacological mode of action. This project will provide significant advances in the field of organocatalysis (new methodology for asymmetric synthesis), natural product synthesis (first preparation of the Daphnezomine L alkaloids) and anticancer medicinal chemistry and pharmacology (exploration and study of biological activities).

Field of science

  • /medical and health sciences/basic medicine/medicinal chemistry
  • /medical and health sciences/basic medicine/pharmacology and pharmacy

Call for proposal

FP7-PEOPLE-2013-IEF
See other projects for this call

Funding Scheme

MC-IEF - Intra-European Fellowships (IEF)

Coordinator

THE CHANCELLOR, MASTERS AND SCHOLARS OF THE UNIVERSITY OF OXFORD
Address
Wellington Square University Offices
OX1 2JD Oxford
United Kingdom
Activity type
Higher or Secondary Education Establishments
EU contribution
€ 221 606,40
Administrative Contact
Gill Wells (Ms.)