A Unified Strategy for the Regiospecific Assembly of Homoallyl-Substituted Butenolides and γ-Hydroxybutenolides: First Synthesis of Luffariellolide

Abstract The first synthesis of the antiinflammatory marine ­natural product luffariellolide has been achieved by a convergent pathway involving sp 3 -sp 3 cross-coupling and silyloxyfuran oxyfunctionalisation as key steps. An illustration of the inherent ­flexibility of this strategy is provided by...

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Veröffentlicht in:Synlett 2006-09, Vol.2006 (15), p.2480-2482
Hauptverfasser: Boukouvalas, John, Robichaud, Joël, Maltais, François
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The first synthesis of the antiinflammatory marine ­natural product luffariellolide has been achieved by a convergent pathway involving sp 3 -sp 3 cross-coupling and silyloxyfuran oxyfunctionalisation as key steps. An illustration of the inherent ­flexibility of this strategy is provided by a simple synthesis of α,β-acariolide and its γ-hydroxylated derivative from a common silyl­oxyfuran precursor.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-949641