Organocatalysis for Natural and Unnatural Product .. (ONUPS)
Organocatalysis for Natural and Unnatural Product Synthesis
Start date: May 21, 2008,
End date: May 20, 2010
"The development of new strategies that allow increasingly rapid access to structural complexity remains one of the fundamental challenge for the chemical sciences. While the total synthesis approach to molecular complexity is generally based on a costly sequence of individual reactions, it is intriguing to consider that biological systems produce elaborate molecules in an economic continuous process, wherein enzymatic transformations are combined in highly regulated catalytic cascades. Therefore in order to improve the production of complex molecules, lessons learned from Nature could be beneficial for the chemical synthesis. Over the past few years, the field of asymmetric organocatalysis has literally exploded. As one of the pioneering groups in the field, the MacMillan group has reported various groundbreaking catalytic asymmetric reactions based on organocatalysts of their original design. In 2005, MacMillan introduced for the first time the concept of enantioselective organo-cascade catalysis, a powerful strategy that provides rapid access to structural complexity from simple starting materials. In this proposal a strategic approach towards a total synthesis of 12-deoxy phorbol is viewed to demonstrate the applicability and the efficiency of cascade catalysis in the context of the total synthesis of natural products. By employing cascade catalysis in the key bond constructing manipulations, the synthesis of 12-deoxy phorbol, should be achieved in only one-third of the steps that had been required for previous synthetic studies of the phorbol skeleton. The return phase will be dedicated to a not less attractive and exciting field of chemistry where the access to structural complexity is also a challenge: the nanotechnology. This stay in the Leigh Group will allow the researcher to transfer her knowledge and expertise acquired in the field of synthetic organic chemistry to the development of the first organocatalytic active template synthesis of rotaxanes."
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