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

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 V. Zhdankin, M. Venkat Ram Reddy

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
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2007.06.099

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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.",

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

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.",

year = "2007",

month = sep,

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doi = "10.1016/j.tet.2007.06.099",

language = "English (US)",

volume = "63",

pages = "9401--9405",

journal = "Tetrahedron",

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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 V.

AU - Reddy, M. Venkat Ram

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.

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.

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SP - 9401

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JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Practical synthesis and applications of benzoboroxoles

Abstract

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