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Practical synthesis and applications of benzoboroxoles |
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| Authors: | Dinara S. Gunasekera Nathan S. Aalderks J. Subash Chandra Christiana A. Maanu Viktor V. Zhdankin |
| Affiliation: | a Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, MN 55812, United States b Department of Pharmacy Practice and Pharmaceutical Sciences, University of Minnesota Duluth, Duluth, MN 55812, United States |
| Abstract: | A convenient one-pot synthesis of benzoboroxoles has been developed via the reaction of o-bromobenzyl alcohols with NaH, nBuLi, and B(OiPr)3 followed by acidic hydrolysis. Applications of these benzoboroxoles have been demonstrated in Pd-catalyzed cross-coupling reactions and the protocol has been extended for the synthesis of a chiral benzoboroxole. Exceptionally short synthesis of a potent antifungal agent AN2690 and several of its analogs has also been realized. |
| Keywords: | Benzoboroxoles Boronic acids Boronate esters C-C bond formation Suzuki-Miyaura cross-coupling Onychomycosis |
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