Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 18, Pages 13030-13041Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01154
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A novel phosphine-catalyzed [2 + 4] annulation reaction was developed for the highly regio- and diastereoselective synthesis of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters. This method involves the reaction of benzofuran-derived azadienes with acidic hydrogen-tethered allyl carbonates and provides moderate to excellent yields under mild reaction conditions. Furthermore, the strategy presented in this study is practical, scalable, and offers a pathway for the synthesis of the core structural motif of the fungistatic drug griseofulvin.
A novel highly regio-and diastereoselective phosphine-catalyzed [2 + 4] annulation of benzofuran-derived azadienes (BDAs) with acidic hydrogen-tethered allyl carbonates has been developed ingeniously. A range of functionalized spiro[benzofuran-cyclohexane] derivatives with two consecutive stereocenters were smoothly obtained in moderate to excellent yields under mild reaction conditions from readily available materials. Moreover, this method is a practical and scalable strategy that creates the core structural motif of the fungistatic drug, griseofulvin.
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