| Abstract
| - A stereoselective synthesis of coronafacic acid, a natural component of the phytotoxin coronatin, wasachieved using an intramolecular Diels−Alder reaction as the key step. The triene precursor bearing asubstituted diene and a vinylketone as dienophile was synthesized and then tested in the thermalintramolecular cyclization. We have devised a new strategy to assemble the E,Z-diene through thestereoselective aldol reaction of an ester enolate followed by a stereoselective dehydration. Followingthe thermal cyclization, the corresponding hydrindanone thereby obtained with the desired relativestereochemistry could easily be converted into the natural product. The synthesis of the coronafacic acidwas accomplished in six steps in 29% overall yield.
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