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A Powerful Enantioselective Organocatalytic Approach to the Total Synthesis of
Madangamine Alkaloids

Objective

"The projet concerns the development of a powerful first total synthesis of the Madagamine alkaloids. The route starts with an organocatalytic enantioselective and diastereoselective Michael addition of cyanoacetate pronucleophiles to a nitrocyclohexene derivative, as a key step to the formation of the ABC core. When the product of this reaction is subjected to a nitro-Mannich, Mannich reaction cascade this should allow us to construct the core of the madangamine alkaloids rapidly, selectively and on scale. The overall synthetic strategy has two parts. The first concerns a fast and enantioselective assembly of diazatricyclic core common to all madangamines (ABC rings). The second concerns easy and efficient ways to build the two macrocyclic rings (D and E rings), which play a fundamental role in their biological activity. The project combines, catalysis, total synthesis, structure elucidation and evaluation of biological properties."

Call for proposal

FP7-PEOPLE-2011-IEF
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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
€ 200 371,80
Administrative Contact
Gill Wells (Ms.)