Synthesis 2013; 45(10): 1414-1420
DOI: 10.1055/s-0032-1316916
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 25 January 2013

Accepted after revision: 15 March 2013

Publication Date:
25 April 2013 (online)


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.

Supporting Information