Studies in multidrug resistance reversal: a rapid and stereoselective synthesis of the dihydroagarofuran ring system |
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Authors: | Christopher A Lee |
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Institution: | Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA |
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Abstract: | Several dihydroagarofuran esters have been reported to be effective multidrug resistance (MDR) reversing agents for both cancer cells and bacteria. We report a rapid synthesis of the dihydroagarofuran ring system from carvone in a sequence that is highlighted by a sequential conjugate addition/aldol sequence, a ring closing metathesis reaction, and a diastereoselective alkene reduction to provide an axial methyl group. The synthesis allows for differential esterification reactions as required to study the roles of these groups in MDR reversal. |
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Keywords: | Multidrug resistance Conjugate addition/aldol Metathesis Acylation |
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