The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates

Ugo Pradere; Herve Clavier; Vincent Roy; Steven P. Nolan; Luigi A. Agrofoglio

doi:10.1002/ejoc.201101111

The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates

Ugo Pradere, Herve Clavier, Vincent Roy, Steven P. Nolan, Luigi A. Agrofoglio

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

18 Citations (Scopus)

Abstract

A short synthetic route to phosphonate prodrugs by olefin cross-metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ruindenylidene catalyst, which bears the N-heterocyclic carbene 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.

Original language	English
Pages (from-to)	7324-7330
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	36
DOIs	https://doi.org/10.1002/ejoc.201101111
Publication status	Published - Dec 2011

Keywords

Medicinal chemistry
Prodrugs
Drug design
Antiviral agents
Meta-thesis
Phosphonate synthons
Acyclonucleoside phosphonates
N-HETEROCYCLIC CARBENES
RING-CLOSING METATHESIS
ACYCLIC NUCLEOSIDE PHOSPHONATES
RUTHENIUM CATALYSTS
ANTIVIRAL ACTIVITY
NUCLEOPHILIC CARBENE
LIGANDS
COMPLEXES
EFFICIENT
BEARING

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10.1002/ejoc.201101111

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title = "The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates",

abstract = "A short synthetic route to phosphonate prodrugs by olefin cross-metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ruindenylidene catalyst, which bears the N-heterocyclic carbene 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.",

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author = "Ugo Pradere and Herve Clavier and Vincent Roy and Nolan, {Steven P.} and Agrofoglio, {Luigi A.}",

year = "2011",

month = dec,

doi = "10.1002/ejoc.201101111",

language = "English",

pages = "7324--7330",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

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T1 - The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates

AU - Pradere, Ugo

AU - Clavier, Herve

AU - Roy, Vincent

AU - Nolan, Steven P.

AU - Agrofoglio, Luigi A.

PY - 2011/12

Y1 - 2011/12

N2 - A short synthetic route to phosphonate prodrugs by olefin cross-metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ruindenylidene catalyst, which bears the N-heterocyclic carbene 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.

AB - A short synthetic route to phosphonate prodrugs by olefin cross-metathesis, which uses either (acyloxymethyl) or (hexadecyloxypropyl) allylphosphonate building blocks is described. A study of eight ruthenium catalysts including the Ruindenylidene catalyst, which bears the N-heterocyclic carbene 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene, was undertaken. This method was applied to the synthesis of acyclonucleoside phosphonate prodrugs. This strategy is appealing for further uses in pharmaceutical and medicinal research.

KW - Medicinal chemistry

KW - Prodrugs

KW - Drug design

KW - Antiviral agents

KW - Meta-thesis

KW - Phosphonate synthons

KW - Acyclonucleoside phosphonates

KW - N-HETEROCYCLIC CARBENES

KW - RING-CLOSING METATHESIS

KW - ACYCLIC NUCLEOSIDE PHOSPHONATES

KW - RUTHENIUM CATALYSTS

KW - ANTIVIRAL ACTIVITY

KW - NUCLEOPHILIC CARBENE

KW - LIGANDS

KW - COMPLEXES

KW - EFFICIENT

KW - BEARING

U2 - 10.1002/ejoc.201101111

DO - 10.1002/ejoc.201101111

M3 - Article

SN - 1434-193X

SP - 7324

EP - 7330

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 36

ER -

The Shortest Strategy for Generating Phosphonate Prodrugs by Olefin Cross-Metathesis - Application to Acyclonucleoside Phosphonates

Abstract

Keywords

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