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A Total Synthesis of Galbonolide B

2007; American Chemical Society; Volume: 72; Issue: 24 Linguagem: Inglês

10.1021/jo701509r

1520-6904

Philip J. Parsons, Lewis E. Pennicott, James J. Eshelby, Matthias Goessman, Adrian J. Highton, Peter B. Hitchcock,

Microbial Natural Products and Biosynthesis

An ester enolate rearrangement/silicon mediated fragmentation cascade was used to convert 7 and 8 into the alcohol 9. The alcohol 9 was converted into the allylic alcohol 12 and then to the ester 14. A further ester enolate rearrangement furnished the stereochemical identity of galbonolide B 1. Base mediated macrocyclization of the acetate ester 16 followed by base mediated alkylation and acetal deprotection gave galbonolide B 1.