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A Total Synthesis of Galbonolide B

journal contribution
posted on 2023-06-07, 20:37 authored by Philip J Parsons, Lewis Pennicott, James Eshelby, Matthias Goessmann, Adrian Highton, Peter Hitchcock
(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

History

Publication status

  • Published

Journal

Journal of Organic Chemistry

ISSN

0022-3263

External DOI

Issue

24

Volume

72

Page range

9387-9390

Department affiliated with

  • Chemistry Publications

Notes

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.

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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