From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues

Paolo Quadrelli; Mariella Mella; Serena Carosso; Bruna Bovio

doi:10.1055/s-0032-1316916

Synthesis, Table of Contents

Synthesis 2013; 45(10): 1414-1420
DOI: 10.1055/s-0032-1316916

paper

From the Ene Reaction of Nitrosocarbonyl Intermediates with 3-Methylbut-2-en-1-ol, a New Class of Purine N,O-Nucleoside Analogues

Paolo Quadrelli*

Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy Email: paolo.quadrelli@unipv.it Fax: +39(0382)987323

,

Mariella Mella

Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy Email: paolo.quadrelli@unipv.it Fax: +39(0382)987323

,

Serena Carosso

Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy Email: paolo.quadrelli@unipv.it Fax: +39(0382)987323

,

Bruna Bovio

Dipartimento di Chimica, Università degli Studi di Pavia, Viale Taramelli 12, 27100 Pavia, Italy Email: paolo.quadrelli@unipv.it Fax: +39(0382)987323

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Abstract

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Abstract

Sterically encumbered nitrosocarbonyl derivatives of mesitylene or anthracene undergo ene reactions with 3-methylbut-2-en-1-ol to give the corresponding the 5-hydroxyisoxazolidine adducts in fair yields. According to the proposed mechanism, these heterocycles are derived from the anti-Markovnikov orientation of the ene reaction. The isoxazolidin-5-yl acetate derivatives are synthons of choice for the preparation of N,O-nucleoside analogues containing purine rings by means of the Vorbrüggen protocol.

Key Words

nucleosides - ene reactions - heterocycles - cyclization

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References

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