One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes

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

Abstract

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of orthofused 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.

Citation

Burroughs, L., Eccleshare, L., Ritchie, J., Kulkarni, O., Lygo, B., Woodward, S., & Lewis, W. (2015). One-pot Cannizzaro cascade synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl aldehydes. Angewandte Chemie International Edition, 54(36), https://doi.org/10.1002/anie.201505347

• Journal Article Type: Article
• Acceptance Date: Jul 29, 2015
• Online Publication Date: Aug 25, 2015
• Publication Date: Sep 1, 2015
• Deposit Date: Sep 28, 2017
• Publicly Available Date: Sep 28, 2017
• Journal: Angewandte Chemie International Edition
• Print ISSN: 1433-7851
• Electronic ISSN: 1521-3773
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 54
• Issue: 36
• DOI: https://doi.org/10.1002/anie.201505347
• Keywords: aldehydes; annulation; carbocycles; medium-ring compounds; ; synthetic methods
• Public URL: https://nottingham-repository.worktribe.com/output/757860
• Publisher URL: http://onlinelibrary.wiley.com/doi/10.1002/anie.201505347/abstract?
• Contract Date: Sep 28, 2017