Journal
HETEROCYCLES
Volume 62, Issue -, Pages 583-618Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-03-S(P)53
Keywords
cycloaddition; synthesis; thionium ion; furan; carbocation
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Certain substituted alkoxyallylic sulfones were alkylated and treated with Lewis acids to produce vinylthionium ions that underwent intramolecular [4+3] cycloaddition reactions with a tethered furan. Manipulation of the cycloadduct led to the synthesis of widdrol. Other attempts to prepare the cycloadducts were made, but none were exceptionally better than the route using vinylthionium ions as intermediates. Interesting aspects of the alkylation chemistry of phenylthio-substituted alkoxyallylic sulfones are detailed as well.
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