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.
Bibliographical noteFunding Information:
This research was supported by grants from Research Corporation (CC6961), and the American Cancer Society (IRG-58-001-46-IRG51). We also thank Department of Chemistry and Biochemistry and College of Pharmacy, University of Minnesota Duluth for the facilities and funding.
Copyright 2009 Elsevier B.V., All rights reserved.
- Boronate esters
- Boronic acids
- C-C bond formation
- Suzuki-Miyaura cross-coupling