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2 results on '"Franco Ghelfi"'

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

Author

Ugo Maria Pagnoni, Ennio Valentin, Fulvia Felluga, Franco Ghelfi, Fabrizio Roncaglia, Mariella Pattarozzi, and Andrew F. Parsons

Subjects
radical reactions, Stereochemistry, cyclizations, eliminations, lactams, lactones, Organic Chemistry, chemistry.chemical_element, Protein tyrosine phosphatase, Pulchellalactam, Copper, Radical cyclization, Catalysis, chemistry, Transition metal, Atom
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.

Published
2007

2. Preparation of the Maleic Anhydride Nucleus from Dichloro ?-Lactams: Focus on the Role of the N-Substituent in the Functional Rearrangement and in the Hydrolytic Steps.

Author

Franco Ghelfi

Subjects
*MALEIC anhydride, *MALEIC acid, *HETEROCYCLIC compounds, *SOLVOLYSIS
Abstract

The preparation of the 3,4-dialkyl-substituted maleic anhydride nucleus, through the functional rearrangement of dichloro ?-lactams, allowed the comparison of various N-substituents in the functional rearrangement step. The 2-pyridyl group proved to be the most appropriate N-substituent for the hydrolysis of the 5-methoxy-1,5-dihydro-2 H-pyrrol-2-one intermediate into the 5-hydroxy adduct, and for the hydrolysis of the maleimide nucleus into the maleic anhydride. The oxidation of the 5-hydroxy-1,5-dihydro-2 H-pyrrol-2-one into the corresponding maleimide was achieved with manganese(IV) oxide. [ABSTRACT FROM AUTHOR]

Published
2008
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