Journal
TETRAHEDRON LETTERS
Volume 45, Issue 19, Pages 3783-3786Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2004.03.085
Keywords
quinine; quinidine; piperidine; cyclopentene-1,3-diol monoacetate; epoxide ring opening
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Disubstituted cyclopentene was prepared from cyclopentene monoacetate and transferred into disubstituted piperidine via oxidative cleavage of the olefin moiety followed by piperidine ring formation. The piperidine was then condensed at the side chain with a quinoline part to afford the olefin precursor of quinine. Finally, the olefin was converted into quinine through the corresponding epoxide. Quinidine was synthesized in a similar way. (C) 2004 Elsevier Ltd. All rights reserved.
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