Gold Catalysed 1,4-Enyne Acetate Strategy for the Synthesis of 1 H -Indenes and Partially Hydrogenated Methanonaphtho[1,2-c]furan-1,3(4 H)-diones

Xiaoyu Chen, Andrew Thomas Holm, Philip Wai Hong Chan

Research output: Contribution to journalArticleResearchpeer-review

Abstract

A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(i)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels-Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an in situ formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels-Alder reaction with maleic anhydride to afford the bridged furan product.

Original languageEnglish
Pages (from-to)1165-1175
Number of pages11
JournalAustralian Journal of Chemistry
Volume73
Issue number12
DOIs
Publication statusPublished - 13 Aug 2020

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