Practical synthesis and applications of benzoboroxoles

Dinara S. Gunasekera, Dennis J. Gerold, Nathan S. Aalderks, J. Subash Chandra, Christiana A. Maanu, Paul Kiprof, Viktor V. Zhdankin, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

33 Citations (Scopus)

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
Pages (from-to)9401-9405
Number of pages5
JournalTetrahedron
Volume63
Issue number38
DOIs
Publication statusPublished - 17 Sep 2007
Externally publishedYes

Keywords

  • Benzoboroxoles
  • Boronate esters
  • Boronic acids
  • C-C bond formation
  • Onychomycosis
  • Suzuki-Miyaura cross-coupling

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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