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A Total Synthesis of Galbonolide B

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posted on 23.11.2007 by Philip J. Parsons, Lewis Pennicott, James Eshelby, Matthias Goessman, Adrian Highton, Peter Hitchcock
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.