Chiral Amide Synthesis

Posted June 28th, 2010 at 11:31 am.

Abstract: Laura Alexander
Mentor: Dr. Malachowski
Enantiomerically pure compounds containing chiral quaternary carbons are rare in nature but have very useful biological activity. By way of the three step Birch-Cope synthesis, these compounds can be synthesized in high yield. The first step of the synthesis is a Birch reduction allylation, which adds a substituent to a tertiary carbon, yielding a quaternary carbon. The second step is an enol ether hydrolysis which forms a carboxylic acid at the 6’ position relative to the quaternary carbon. The final step is a Cope rearrangement which transfers the organic substituent added in the Birch reduction-allylation to the 3’ carbon relative to the original quaternary carbon, using the previous structure. By removing the substituent from the quaternary carbon, a tertiary carbon is created and a new quaternary carbon is created.

Using this scheme, (+)-lycoramine, a derivative of a drug approved for the treatment of Alzheimer’s disease, has been synthesized. It is hopeful that other biologically active drugs may be synthesized as well.

Filed under: 2010,Alexander, Laura,Malachowski, Dr. William Tags: by Lisa Klinman

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