Total Synthesis of the Purported Structure of Sclerophytin F

The synthesis of
the compound that has been proposed to be the
natural product sclerophytin F has been completed from a known vinylogous
carbonate. The synthetic strategy relied upon rearrangement of a catalytically
generated ylide-like intermediate to produce an oxa­bicyclo­[6.2.1]-5-undecen-9-one
and an intermolecular Diels–Alder reaction to construct the
complete tricyclic core found in the natural product. Comparison of
the spectroscopic data for synthetic material to that reported for
sclerophytin F shows that the natural product does not have the revised
structure possessing the 3S configuration (*) proposed
previously.