Rh(I)-catalyzed ring opening of an IMDAF-derived oxabicyclo cycloadduct as the key step in the synthesis of (+/-)-epi-zephyranthine.
[reaction: see text] A new strategy for epi-zephyranthine has been developed that is based in part on an extraordinarily facile intramolecular Diels-Alder reaction of a 2-imido-substituted furan. By using a Rh(I)-catalyzed ring opening of the resulting oxabicyclic adduct, the cis-diol stereochemistry of epi-zephyranthine was established.
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