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Synthesis of furan-bridged 10-membered rings through [8 + 2]-cycloaddition of dienylfurans and acetylenic esters

Zhang, Lei; Wang, Yu; Buckingham, Clare; Herndon, James W
[reaction: see text] The coupling of various dienylfurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases this reaction proceeds via [8 + 2]-cycloaddition to afford furan-bridged 10-membered ring systems as a single diastereomer. Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene.
PMID: 15816778
ISSN: 1523-7060
CID: 5339952