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RESEARCH ARTICLE
Contents Vol 73(12)

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

Xiaoyu Chen A C , Andrew Thomas Holm A C and Philip Wai Hong Chan https://orcid.org/0000-0002-8786-6143 A B D
+ Author Affiliations
- Author Affiliations

A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.

B Department of Chemistry, University of Warwick, Coventry CV4 7AL, UK.

C These authors contributed equally to this work.

D Corresponding author. Email: phil.chan@monash.edu

Australian Journal of Chemistry 73(12) 1165-1175 https://doi.org/10.1071/CH20175
Submitted: 31 May 2020  Accepted: 6 July 2020   Published: 13 August 2020

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.


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