Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

L A  Agrofoglio; F  Amblard; Steven Patrick Nolan; S  Charamon; I  Gillaizeau; T A  Zevaco; P  Guenot

doi:10.1016/j.tet.2004.07.009

Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

L A Agrofoglio, F Amblard, Steven Patrick Nolan, S Charamon, I Gillaizeau, T A Zevaco, P Guenot

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

Abstract

The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	8397-8404
Number of pages	8
Journal	Tetrahedron
Volume	60
Issue number	38
DOIs	https://doi.org/10.1016/j.tet.2004.07.009
Publication status	Published - 13 Sept 2004

Keywords

metathesis
palladium
nucleosides
allylic alkylation
CARBOCYCLIC NUCLEOSIDES
ENANTIOSELECTIVE SYNTHESIS
OLEFIN METATHESIS
CLOSURE METATHESIS
ANTIVIRAL ACTIVITY
CROSS-METATHESIS
ANALOGS
VIRUS
COMPLEXES
(-)-ARISTEROMYCIN

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title = "Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies",

abstract = "The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.",

keywords = "metathesis, palladium, nucleosides, allylic alkylation, CARBOCYCLIC NUCLEOSIDES, ENANTIOSELECTIVE SYNTHESIS, OLEFIN METATHESIS, CLOSURE METATHESIS, ANTIVIRAL ACTIVITY, CROSS-METATHESIS, ANALOGS, VIRUS, COMPLEXES, (-)-ARISTEROMYCIN",

author = "Agrofoglio, \{L A\} and F Amblard and Nolan, \{Steven Patrick\} and S Charamon and I Gillaizeau and Zevaco, \{T A\} and P Guenot",

year = "2004",

month = sep,

day = "13",

doi = "10.1016/j.tet.2004.07.009",

language = "English",

volume = "60",

pages = "8397--8404",

journal = "Tetrahedron",

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publisher = "Elsevier",

number = "38",

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TY - JOUR

T1 - Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

AU - Agrofoglio, L A

AU - Amblard, F

AU - Nolan, Steven Patrick

AU - Charamon, S

AU - Gillaizeau, I

AU - Zevaco, T A

AU - Guenot, P

PY - 2004/9/13

Y1 - 2004/9/13

N2 - The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.

AB - The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.

KW - metathesis

KW - palladium

KW - nucleosides

KW - allylic alkylation

KW - CARBOCYCLIC NUCLEOSIDES

KW - ENANTIOSELECTIVE SYNTHESIS

KW - OLEFIN METATHESIS

KW - CLOSURE METATHESIS

KW - ANTIVIRAL ACTIVITY

KW - CROSS-METATHESIS

KW - ANALOGS

KW - VIRUS

KW - COMPLEXES

KW - (-)-ARISTEROMYCIN

UR - https://www.scopus.com/pages/publications/4444272887

U2 - 10.1016/j.tet.2004.07.009

DO - 10.1016/j.tet.2004.07.009

M3 - Article

SN - 0040-4020

VL - 60

SP - 8397

EP - 8404

JO - Tetrahedron

JF - Tetrahedron

IS - 38

ER -

Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

Abstract

Keywords

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