Brønsted acid catalyzed [4 + 2] cycloaddition for the synthesis of bisbenzannulated spiroketals with antifungal activities.

Org Biomol Chem

Shanghai Key Laboratory of Chemical Biology & School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

Published: June 2024


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Article Abstract

The intermolecular [4 + 2] cycloaddition of -hydroxy benzyl alcohols with isochroman ketals was realized by CFCOH catalysis. A broad range of bisbenzannulated [6,6]-spiroketals were formed under the metal-free mild conditions in moderate to excellent yields (45-98%) with mostly excellent diastereoselectivities (up to >20 : 1 dr). Furthermore, the enantioselective version was also preliminarily investigated and the bisbenzannulated [6,6]-spiroketal was obtained with 61% ee in the presence of Sc(OTf)/Feng's chiral ,'-dioxide ligand. Some of the bisbenzannulated [6,6]-spiroketal products showed good antifungal activities against and .

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http://dx.doi.org/10.1039/d4ob00584hDOI Listing

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