A Total Synthesis of Galbonolide B

Parsons, Philip J, Pennicott, Lewis, Eshelby, James, Goessmann, Matthias, Highton, Adrian and Hitchcock, Peter (2007) A Total Synthesis of Galbonolide B. Journal of Organic Chemistry, 72 (24). pp. 9387-9390. ISSN 0022-3263

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(Chemical Equation Presented) 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

Item Type: Article
Additional Information: A novel approach to the synthesis of Galbonolide, all synthetic work carried at Sussex in the laboratory of the principle and corresponding author PJP. The project also involved, two industrial collaborators as co authors.
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Philip Parsons
Date Deposited: 06 Feb 2012 18:35
Last Modified: 19 Mar 2012 11:27
URI: http://sro.sussex.ac.uk/id/eprint/17265
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