A Nitrile Oxide Cycloaddition Approach to (-)-Pyrenophorin, and Rosefuran.

Article abstract of DOI:10.1016/0040-4020(95)00392-L

<3+2> Nitrile oxide cycloaddition chemistry has been conveniently applied as carbon-carbon bond forming reaction for the assemblage of the functionalized carbon atom fragments required for the synthesis of two simple but different targets such as the macrolide antibiotic (-)-pyrenophorin 1 and rosefuran 2, a trace component of the high prized oil of rose.In both cases, an intermediate 3,5-disubstituted isoxazoline ring system has been used as serviceable precursor of the the salient structural feature of the targets, namely a γ-oxoacrylate moiety, common to many biologically active compounds, and a β,γ-dihydroxyketone functionality, easily converted by mild acid treatment to rosefuran.