A [3-NITRILE OXIDE CYCLOADDITION APPROACH TO (-)-PYRENOPHORIN, AND ROSEFURAN(2])

[3+2] Nitrile oxide cycloaddition chemistry has been conveniently appl ied as carbon-carbon bond forming reaction for the assemblage of the f unctionalized carbon atom fragments required for the synthesis of two simple but different targets such as the macrolide antibiotic (-)-pyre nophorin 1 and rosefuran 2, a trace component of the high prized oil o f rose. In both cases, an intermediate 3,5-disustituted isoxazoline ri ng system has been used as serviceable precursor of the the salient st ructural feature of the targets, namely a gamma-oxoacrylate moiety, co mmon to many biologically active compounds, and a beta,gamma-dihydroxy ketone functionality, easily converted by mild acid treatment to rosef uran.