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

Authors :
Ugo Maria Pagnoni
Ennio Valentin
Fulvia Felluga
Franco Ghelfi
Fabrizio Roncaglia
Mariella Pattarozzi
Andrew F. Parsons
Source :
Synthesis. 2007:1882-1886
Publication Year :
2007
Publisher :
Georg Thieme Verlag KG, 2007.

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.

Details

ISSN :
1437210X and 00397881
Volume :
2007
Database :
OpenAIRE
Journal :
Synthesis
Accession number :
edsair.doi.dedup.....0dc20c2825729f2f6a28353e0d0b3784