Implementing the Birch-Cope Sequence and Rearrangement for the Synthesis of Natural Therapies

Posted May 14th, 2010 at 2:28 pm.

Sharan Kaur Mehta

Mentor: Dr. Malachowski

Within the scope of organic synthesis, the goal of attaining biologically active compounds has proven its extensive value as well as its array of strategic challenges, specifically in the creation of enantiomerically pure carbocyclic quaternary stereocenters. However, the implementation of the three-stage Birch-Cope sequence, comprising of the Birch reduction-allylation, enol ether hydrolysis, and Cope rearrangement has become a proven method of effectively generating such chiral stereocenters, which are crucial synthetic intermediates. Expanding on the procedure’s prior successes, its discovery has stimulated a wealth of synthetic opportunity in the ultimate hopes of developing innovative therapies in the way of antibiotics, which the Malachowski research team currently seeks to explore. Within the scheme of the project, my role this summer specifically involves the production of the o-anisic acid derivative starting material possessing a chiral auxiliary, which is derived from a reaction with L-prolinol. Longer range goals include conducting the Birch-Cope sequence and contributing to the exploration of the product after the Cope rearrangement.

Synthesis of o-anisic acid derivative with chiral auxiliary:

mehta1

Birch-Cope Sequence and Rearrangement:

mehta2

Filed under: 2009,Malachowski, Dr. William,Mehta, Sharan by Ann Dixon

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