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

doi:10.1016/j.tet.2007.06.099

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

38 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 language	English (US)
Pages (from-to)	9401-9405
Number of pages	5
Journal	Tetrahedron
Volume	63
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2007.06.099
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

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title = "Practical synthesis and applications of benzoboroxoles",

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.",

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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.",

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T1 - Practical synthesis and applications of benzoboroxoles

AU - Gunasekera, Dinara S.

AU - Gerold, Dennis J.

AU - Aalderks, Nathan S.

AU - Chandra, J. Subash

AU - Maanu, Christiana A.

AU - Kiprof, Paul

AU - Zhdankin, Viktor

AU - Mereddy, Venkatram R

N1 - 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.

PY - 2007/9/17

Y1 - 2007/9/17

N2 - 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.

AB - 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.

KW - Benzoboroxoles

KW - Boronate esters

KW - Boronic acids

KW - C-C bond formation

KW - Onychomycosis

KW - Suzuki-Miyaura cross-coupling

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SP - 9401

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JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Practical synthesis and applications of benzoboroxoles

Abstract

Bibliographical note

Keywords

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