Triflic Anhydride-Mediated Approach to Furo[3,2-]furans from Diacetonide Protected Furanoses.

J Org Chem

Natural Products and Medicinal Chemistry Division, CSIR-Indian Institute of Integrative Medicine, Canal Road, Jammu, Jammu and Kashmir 180001, India.

Published: September 2024

Trifluoromethanesulfonic anhydride (TfO) exhibits excellent reactivity as an electrophile, serving as a highly versatile reagent in diverse chemical transformations. Herein, we report an operationally simple, efficient, unique, and practical one-step strategy for synthesizing diverse valuable structures bearing furo[3,2-]furans core leveraging TfO's promoted reactivity of nitriles with diacetonide protected furanose. Furthermore, we demonstrate the potential of furo[3,2-]furan as a precursor for complex structures through 1,3-dipolar cycloaddition.

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http://dx.doi.org/10.1021/acs.joc.4c01067DOI Listing

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