A [3+2]nitrile oxide cycloaddition approach to (−)-pyrenophorin, and rosefuran

Add time:07/12/2019    Source:sciencedirect.com

[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-disustituted 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.

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