ORGN 1005 |
| An efficient new method to synthesize α-oxy N-acyl aminals and hemiaminals in a single step from readily synthesized N-acyl enamines has been developed using PhI(OAc)2 as the oxidant. The reaction conditions are very mild and the products are obtained in good yields (65-92%). This method not only provides quick access to N-acyl aminals and hemiaminals which normally requires several chemical transformations with reported procedures, but also generates substituted tetrahydropyrans with functionality at the C2 position available for further chemical transformation. A possible reaction pathway is laid out and preliminary results support a radical cation process when the reaction is carried out in protic non-nucleophilic polar solvents. The application of this new methodology to the total synthesis of pederin family of natural products such as psymberin will be discussed.
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Total Synthesis of Complex Molecules
1:00 PM-4:20 PM, Thursday, August 23, 2007 BCEC -- 258A, Oral
Division of Organic Chemistry |
