Efficient Syntheses of New 2,2′-Disubstituted-2,3-dihydrofuran Derivatives and Natural Polyketide Analogues

Abstract

Efficient syntheses of new 2,2′-disubstituted-2,3-dihydrofuran(5H)-4-one,spiro{benzofuran-2,2′-bicyclo[2.2.1]heptan}-4(5H)-one derivatives, and natural polyketide analogues have been achieved via the oxidative [3 + 2] cycloaddition of 1,3-dicarbonyl compounds with monoterpenes myrcene, camphene, and natural phenyl propenes, namely anethole and safrole respectively. Interestingly, the reaction of isoprene and myrcene with 1,3-dicarbonyl compounds yielded 2,2-disubstituted tetrahydrobenzofuran-4(5H)-one derivatives at room temperature. Thus, several substituted 2,3-dihydrofuran derivatives (3a–3h) with potential biological activity have been synthesized.

GRAPHICAL ABSTRACT

Keywords:

• 2,2′-Disubstituted-2,3-dihydrohydrofurans
• natural polyketide analogues
• oxidative [3 + 2] cycloaddition
• spiro{benzofuran-2,2′-bicyclo[2.2.1]heptan}-4(5H)-one derivatives

ACKNOWLEDGMENTS

We are grateful to Kelkar Education Trust, Mumbai, for encouragement and support. We are also thankful to the Department of Chemistry and Sophisticated Analytical Instrumentation Facility, Indian Institute of Technology, Bombay, and Tata Institute of Fundamental Research, Mumbai, for NMR spectral data.