Rapid Access to 2-Methylene Tetrahydrofurans and γ-Lactones: A Tandem Four-Step Process.

Angew Chem Int Ed Engl

School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, China.

Published: February 2016

A one-pot tandem process involving hydrolysis, Knoevenagel condensation, Michael addition, and Conia-ene (HKMC) reactions has been developed for the rapid synthesis of indanone-fused 2-methylene tetrahydrofurans from the reaction of enynals and propynols. In this process, two rings and four bonds are generated with 100 % atom-economy and high step-efficiency. The resulting tetrahydrofurans were readily oxidized into α-methylene γ-lactones, which are one of the most important substructures in natural and bioactive compounds.

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Source
http://dx.doi.org/10.1002/anie.201511133DOI Listing

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