A Convenient Synthesis of New Purinyl-homo-carbonucleosides on a Cyclopentane Ring Fused with Pyridazine

Olga Caamaño; Generosa Gómez; Franco Fernández; Marcos Daniel García; Xerardo García-Mera; Eric De Clercq

doi:10.1055/s-2004-834870

PAPER

A Convenient Synthesis of New Purinyl-homo-carbonucleosides on a Cyclopentane Ring Fused with Pyridazine

Olga Caamaño*^a, Generosa Gómez*^b, Franco Fernández^a, Marcos Daniel García^a, Xerardo García-Mera^a, Eric De Clercq^c
^a Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
Fax: +34(981)594912; e-Mail: qoolga@usc.es;
^b Departamento de Química Orgánica, Facultade de Química, Lagoas-Marcosende, Universidade de Vigo, 36200 Vigo, Spain
Fax: +34(986)813663; e-Mail: ggomez@uvigo.es.;
^c Rega Institute for Medical Research, Katholieke Universiteit Leuven, 3000 Leuven, Belgium

Abstract

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Abstract

The new purinyl homo-carbonucleosides 10 and 17a were prepared from 1,4-diphenyl-5,8-dihydro-5,8-methanophthalazine by one-pot ozonolysis and reductive cleavage, followed by monoprotection with an Ac or TBDMS group, mesylation of the resulting diol and replacement of the mesyl group with 6-chloropurine in the presence of NaH and 18-crown-6 ether. Homo-carbonucleosides 12 and 13 were then obtained from 10 by substitution of the chlorine in purine position 6. Compounds 17b and 19 were obtained from 17a in the same way.

Key words

ozonolysis - acylation - diols - carbocyclic nucleosides - heterocycles - pyridazine

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