Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Stephen Hanessian; Juan Pablo Maianti; Rowena D. Matias; Lee Ann Feeney; Eliana S. Armstrong

doi:10.1021/ol2027703

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Stephen Hanessian
, Juan Pablo Maianti
, Rowena D. Matias
, Lee Ann Feeney
, Eliana S. Armstrong

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

20 Scopus citations

Abstract

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd ₂(dba) ₃ and Bu ₃P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

Original language	English (US)
Pages (from-to)	6476-6479
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	24
DOIs	https://doi.org/10.1021/ol2027703
State	Published - Dec 16 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol2027703

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title = "Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation",

abstract = "Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol \% Pd 2(dba) 3 and Bu 3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.",

author = "Stephen Hanessian and Maianti, \{Juan Pablo\} and Matias, \{Rowena D.\} and Feeney, \{Lee Ann\} and Armstrong, \{Eliana S.\}",

year = "2011",

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doi = "10.1021/ol2027703",

language = "English (US)",

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AU - Hanessian, Stephen

AU - Maianti, Juan Pablo

AU - Matias, Rowena D.

AU - Feeney, Lee Ann

AU - Armstrong, Eliana S.

PY - 2011/12/16

Y1 - 2011/12/16

N2 - Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd 2(dba) 3 and Bu 3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

AB - Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd 2(dba) 3 and Bu 3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

UR - https://www.scopus.com/pages/publications/84055213972

UR - https://www.scopus.com/pages/publications/84055213972#tab=citedBy

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JO - Organic Letters

JF - Organic Letters

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ER -

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Abstract

ASJC Scopus subject areas

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