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Synthesis 1999; 1999(5): 821-828
DOI: 10.1055/s-1999-3482
DOI: 10.1055/s-1999-3482
paper
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Synthesis of Racemic Frenolicin B and 5-epi-Frenolicin B via Intramolecular Palladium Catalyzed Aryloxycarbonylation
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Publication History
Publication Date:
31 December 1999 (online)
A synthesis of the pyranonaphthoquinone antibiotic (±)-frenolicin B[(±)-1] is described. Key step is the intramolecular palladium-catalyzed aryloxycarbonylation of the 2-allyl-1-naphthol derivatives 8a,b to give the tricyclic λ-lactones 6a,b. Only the former (6a) is converted successfully into (±)-deoxyfrenolicin, the immediate precursor of (±)-1.
rac-frenolicin B - rac-5-epi-frenolicin B - rac-deoxyfrenolicin - palladium-catalyzed aryloxycarbonylation