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

39 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",

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day = "17",

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

language = "English (US)",

volume = "63",

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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.

UR - https://www.scopus.com/pages/publications/34547577782

UR - https://www.scopus.com/pages/publications/34547577782#tab=citedBy

U2 - 10.1016/j.tet.2007.06.099

DO - 10.1016/j.tet.2007.06.099

M3 - Article

AN - SCOPUS:34547577782

SN - 0040-4020

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SP - 9401

EP - 9405

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Practical synthesis and applications of benzoboroxoles

Abstract

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