Development of the claisen rearrangement/organocatalytic diels-alder approach for the synthesis of eunicellins

Joel F. Hooper, Jonathan M. White, Andrew Bruce Holmes

Research output: Contribution to journalArticleOtherpeer-review

4 Citations (Scopus)

Abstract

The intramolecular Diels-Alder approach to synthesizing eunicellins has proved to be a powerful method for the synthesis of this class of natural products. The key to the success of this strategy is control over the endo/exo selectivity of the cycloaddition reaction, which we have addressed through an organocatalytic reaction employing the MacMillan imidazolidinone catalyst. This approach has been further developed to address the issue of functionality at the C8 position, and a novel scalable method for the extension of the medium-ring lactone has been developed.

Original languageEnglish
Pages (from-to)1189-1194
Number of pages6
JournalAustralian Journal of Chemistry
Volume67
Issue number8-9
DOIs
Publication statusPublished - 2014
Externally publishedYes

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