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.
Original language | English (US) |
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Pages (from-to) | 9401-9405 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 63 |
Issue number | 38 |
DOIs | |
State | Published - Sep 17 2007 |
Bibliographical note
Funding 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:
Copyright 2009 Elsevier B.V., All rights reserved.
Keywords
- Benzoboroxoles
- Boronate esters
- Boronic acids
- C-C bond formation
- Onychomycosis
- Suzuki-Miyaura cross-coupling