Practical synthesis and applications of benzoboroxoles

Dinara S. Gunasekera, Dennis J. Gerold, Nathan S. Aalderks, J. Subash Chandra, Christiana A. Maanu, Paul Kiprof, Viktor Zhdankin, Venkatram R Mereddy

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

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 languageEnglish (US)
Pages (from-to)9401-9405
Number of pages5
JournalTetrahedron
Volume63
Issue number38
DOIs
StatePublished - 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

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