A total synthesis of the hypocholesterolemic agent compactin is described in which the hexahydronaphthalene portion of this molecule is constructed by an intramolecular nitrile oxide cycloaddition reaction. In the context of this synthesis, the isoxazoline ring system was found to serve as a useful 1,3-diene equivalent. The protocol developed for this conversion involves transformation of the isoxazoline to an allylic alcohol followed by regioselective dehydration using aluminum oxide. Molecular mechanics calculations on compactin-related octahydro-naphthisoxazoles are also presented.
ASJC Scopus subject areas
- Organic Chemistry