A Novel Short Approach to (Z)-Pulchellalactam through Transition-Metal-Catalyzed Atom-Transfer Radical Cyclization of 1-Isopropylprop-2-enyl Dichloroacetate

Fulvia Felluga; Franco Ghelfi; Ugo M. Pagnoni; Andrew F. Parsons; Mariella Pattarozzi; Fabrizio Roncaglia; Ennio Valentin

doi:10.1055/s-2007-983709

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Synthesis 2007(12): 1882-1886
DOI: 10.1055/s-2007-983709

PAPER

A Novel Short Approach to (Z)-Pulchellalactam through Transition-Metal-Catalyzed Atom-Transfer Radical Cyclization of 1-Isopropylprop-2-enyl Dichloroacetate

Fulvia Felluga^a, Franco Ghelfi*^b, Ugo M. Pagnoni^b, Andrew F. Parsons^c, Mariella Pattarozzi^d, Fabrizio Roncaglia*^b, Ennio Valentin^a
^a Dipartimento di Scienze Chimiche, Università di Trieste, via Licio Giorgieri 1, 34127 Trieste, Italy
^b Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, via Campi 183, 41100 Modena, Italy
Fax: +39(59)373543; e-Mail: ghelfi.franco@unimore.it; e-Mail: roncaglia.fabrizio@unimore.it;
^c Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
^d Dipartimento di Scienze Chimiche, Università degli Studi di Padova, via Marzolo 1, 35131 Padova, Italy

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Publication History

Received 27 March 2007
Publication Date:
08 June 2007 (online)

Abstract
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Abstract

A new, five-step route to (Z)-pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor, is presented. Key steps are the copper(I) chloride-bipyridyl catalyzed atom-transfer radical cyclization of an appropriate allyl α,α-dichloroacetate and the subsequent dehydrochlorination/prototropic rearrangement of the resulting dichlorolactone.

Key words

cyclizations - eliminations - lactams - lactones - radical reactions

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