Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

Olaf R. Ludek; Tobias Krämer; Jan Balzarini; Chris Meier

doi:10.1055/s-2006-926411

Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

Olaf R. Ludek, Tobias Krämer, Jan Balzarini, Chris Meier^*

^*Corresponding author for this work

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

26 Citations (Scopus)

Abstract

A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.

Original language	English
Pages (from-to)	1313-1324
Number of pages	12
Journal	Synthesis
Issue number	8
DOIs	https://doi.org/10.1055/s-2006-926411
Publication status	Published - Apr 2006

Keywords

Carbocycles
Hydroborations
Mitsunobu reaction
Nucleosides
Stereoselective synthesis

ASJC Scopus subject areas

Organic Chemistry

UN SDGs

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

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10.1055/s-2006-926411

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title = "Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs",

abstract = "A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.",

keywords = "Carbocycles, Hydroborations, Mitsunobu reaction, Nucleosides, Stereoselective synthesis",

author = "Ludek, {Olaf R.} and Tobias Kr{\"a}mer and Jan Balzarini and Chris Meier",

year = "2006",

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doi = "10.1055/s-2006-926411",

language = "English",

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journal = "Synthesis",

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T1 - Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

AU - Ludek, Olaf R.

AU - Krämer, Tobias

AU - Balzarini, Jan

AU - Meier, Chris

PY - 2006/4

Y1 - 2006/4

N2 - A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.

AB - A new divergent approach towards carbocyclic α-, iso- and 3′-epi-nucleosides starting from enantiomerically pure (1S,2R)-2-benzyloxymethylcyclopent-3-enol (5) is described. In the key step, isomeric cyclopentanols were condensed with a N3-protected pyrimidine nucleobase using a modified Mitsunobu protocol. Moreover, the conversion into the cycloSal-pronucleotides and the effect of the orientation of the nucleobase on anti-HIV activity are reported.

KW - Carbocycles

KW - Hydroborations

KW - Mitsunobu reaction

KW - Nucleosides

KW - Stereoselective synthesis

UR - http://www.scopus.com/inward/record.url?scp=33646240368&partnerID=8YFLogxK

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DO - 10.1055/s-2006-926411

M3 - Article

AN - SCOPUS:33646240368

SN - 0039-7881

SP - 1313

EP - 1324

JO - Synthesis

JF - Synthesis

IS - 8

ER -

Divergent synthesis and biological evaluation of carbocyclic α-, iso- and 3′-epi-nucleosides and their lipophilic nucleotide prodrugs

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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