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.