Synthesis of (3R*,4R*)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer and their inhibitory action against influenza virus sialidases

Sean A. Kerrigan; Robin G. Pritchard; Paul W. Smith; Richard J. Stoodley

doi:10.1016/S0040-4039(01)01605-7

Synthesis of (3R,4R)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S,4R)-isomer and their inhibitory action against influenza virus sialidases

Sean A. Kerrigan
, Robin G. Pritchard
, Paul W. Smith
, Richard J. Stoodley

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

Abstract

(3R*,4R*)-4-Acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer are synthesised in five steps from the Diels-Alder cycloadduct of (E)-1-acetoxy-3-methylbuta-1,3-diene and nitroethene; the former acid is a moderately potent inhibitor of influenza A sialidase. © 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	7687-7690
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	43
DOIs	https://doi.org/10.1016/S0040-4039(01)01605-7
Publication status	Published - 22 Oct 2001

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 3 Good Health and Well-being

Keywords

Antivirals
Diels-Alder reactions
Nitro compounds
Oxidation (allylic)

Access to Document

10.1016/S0040-4039(01)01605-7

Cite this

@article{0d355eeea71c43c79ef1836c11e3a8a6,

title = "Synthesis of (3R*,4R*)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer and their inhibitory action against influenza virus sialidases",

abstract = "(3R*,4R*)-4-Acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer are synthesised in five steps from the Diels-Alder cycloadduct of (E)-1-acetoxy-3-methylbuta-1,3-diene and nitroethene; the former acid is a moderately potent inhibitor of influenza A sialidase. {\textcopyright} 2001 Elsevier Science Ltd. All rights reserved.",

keywords = "Antivirals, Diels-Alder reactions, Nitro compounds, Oxidation (allylic)",

author = "Kerrigan, \{Sean A.\} and Pritchard, \{Robin G.\} and Smith, \{Paul W.\} and Stoodley, \{Richard J.\}",

year = "2001",

month = oct,

day = "22",

doi = "10.1016/S0040-4039(01)01605-7",

language = "English",

volume = "42",

pages = "7687--7690",

journal = "Tetrahedron Letters",

issn = "1873-3581",

publisher = "Elsevier BV",

number = "43",

}

Synthesis of (3R*,4R*)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer and their inhibitory action against influenza virus sialidases. / Kerrigan, Sean A.; Pritchard, Robin G.; Smith, Paul W. et al.
In: Tetrahedron Letters, Vol. 42, No. 43, 22.10.2001, p. 7687-7690.

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

TY - JOUR

T1 - Synthesis of (3R*,4R*)-4-acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer and their inhibitory action against influenza virus sialidases

AU - Kerrigan, Sean A.

AU - Pritchard, Robin G.

AU - Smith, Paul W.

AU - Stoodley, Richard J.

PY - 2001/10/22

Y1 - 2001/10/22

N2 - (3R*,4R*)-4-Acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer are synthesised in five steps from the Diels-Alder cycloadduct of (E)-1-acetoxy-3-methylbuta-1,3-diene and nitroethene; the former acid is a moderately potent inhibitor of influenza A sialidase. © 2001 Elsevier Science Ltd. All rights reserved.

AB - (3R*,4R*)-4-Acetylamino-3-(pent-3-oxy)cyclohex-1-ene-1-carboxylic acid and its (3S*,4R*)-isomer are synthesised in five steps from the Diels-Alder cycloadduct of (E)-1-acetoxy-3-methylbuta-1,3-diene and nitroethene; the former acid is a moderately potent inhibitor of influenza A sialidase. © 2001 Elsevier Science Ltd. All rights reserved.

KW - Antivirals

KW - Diels-Alder reactions

KW - Nitro compounds

KW - Oxidation (allylic)

U2 - 10.1016/S0040-4039(01)01605-7

DO - 10.1016/S0040-4039(01)01605-7

M3 - Article

SN - 1873-3581

VL - 42

SP - 7687

EP - 7690

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 43

ER -