Towards the total synthesis of 14-acetoxygelsenicine and synthesis of largazole analogs
Date
2009
Authors
Newkirk, Tenaya L., author
Williams, Robert M., advisor
Stermitz, Frank R., committee member
Ferreira, Eric M., committee member
Rickey, Dawn, committee member
Thamm, Douglas H., committee member
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Abstract
Herein are documented our efforts in two projects, beginning with studies towards the total synthesis of 14-acetoxygelsenicine. We have developed different strategies towards this complex natural product, wherein we have developed routes towards an appropriate substrate for a novel, intramolecular hetero Diels-Alder cyclization. The developed route would also lead to related members of this family of alkaloids, and helps set the stage for future efforts. In the second project discussed, we have successfully pursued the synthesis of numerous, biologically active analogs of the natural product (+)-largazole. Synthetic efforts have led to the design of inhibitors with unprecedented biological activity, as well as providing information regarding the structure-activity relationship of these molecules.
Description
Rights Access
Subject
Alkaloids -- Synthesis
Diels-Alder reaction