Journal
TETRAHEDRON LETTERS
Volume 45, Issue 39, Pages 7193-7196Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.08.041
Keywords
multidrug resistance; conjugate addition/aldol; metathesis; acylation
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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. (C) 2004 Elsevier Ltd. All rights reserved.
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