Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

F Amblard; Steven Patrick Nolan; RF Schinazi; LA Agrofoglio

doi:10.1016/j.tet.2004.11.019

Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

F Amblard, Steven Patrick Nolan, RF Schinazi, LA Agrofoglio

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

Abstract

Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	537-544
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	3
DOIs	https://doi.org/10.1016/j.tet.2004.11.019
Publication status	Published - 17 Jan 2005

Keywords

ACYCLIC NUCLEOSIDE ANALOGS
ANTI-DNA VIRUS
OLEFIN METATHESIS
ORGANOBORON DERIVATIVES
ANTIVIRAL ACTIVITIES
COUPLING REACTION
9-(2-HYDROXYETHOXYMETHYL)GUANINE
INHIBITION
CHEMISTRY
AGENT

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10.1016/j.tet.2004.11.019

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title = "Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies",

abstract = "Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.",

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author = "F Amblard and Nolan, {Steven Patrick} and RF Schinazi and LA Agrofoglio",

year = "2005",

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doi = "10.1016/j.tet.2004.11.019",

language = "English",

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T1 - Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

AU - Amblard, F

AU - Nolan, Steven Patrick

AU - Schinazi, RF

AU - Agrofoglio, LA

PY - 2005/1/17

Y1 - 2005/1/17

N2 - Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

AB - Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

KW - ACYCLIC NUCLEOSIDE ANALOGS

KW - ANTI-DNA VIRUS

KW - OLEFIN METATHESIS

KW - ORGANOBORON DERIVATIVES

KW - ANTIVIRAL ACTIVITIES

KW - COUPLING REACTION

KW - 9-(2-HYDROXYETHOXYMETHYL)GUANINE

KW - INHIBITION

KW - CHEMISTRY

KW - AGENT

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U2 - 10.1016/j.tet.2004.11.019

DO - 10.1016/j.tet.2004.11.019

M3 - Article

SN - 0040-4020

VL - 61

SP - 537

EP - 544

JO - Tetrahedron

JF - Tetrahedron

IS - 3

ER -

Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

Abstract

Keywords

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