One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes

Laurence Burroughs; Lee Eccleshare; John Ritchie; Omkar Kulkarni; Barry Lygo; Simon Woodward; William Lewis

doi:10.1002/anie.201505347

One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes

Angew Chem Int Ed Engl. 2015 Sep 1;54(36):10648-51. doi: 10.1002/anie.201505347. Epub 2015 Jul 29.

Authors

Laurence Burroughs¹, Lee Eccleshare¹, John Ritchie¹, Omkar Kulkarni¹, Barry Lygo¹, Simon Woodward², William Lewis¹

Affiliations

¹ School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK).
² School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD (UK). [email protected].

Abstract

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.

Keywords: aldehydes; annulation; carbocycles; medium-ring compounds; synthetic methods.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.