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J Org Chem. 2005 May 27;70(11):4542-5.

Remote stereocontrol in the Nazarov reaction: a new approach to the core of roseophilin.

Author information

  • 1Dipartimento di Chimica Organica U. Schiff, Polo Scientifico-Universit√† di Firenze, Via della Lastruccia 13, I-50019 Sesto Fiorentino, Italy. ernesto.occhiato@unifi.it

Abstract

Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

PMID:
15903343
DOI:
10.1021/jo0504058
[PubMed - indexed for MEDLINE]
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