The Dowd–Beckwith Reaction: History,Strategies, and Synthetic Potential |
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Authors: | Tushar Singha Abdur Rouf Samim Mondal Suparnak Midya Dr Durga Prasad Hari |
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Institution: | Department of Organic Chemistry, Indian Institute of Scienece, Bangalore, 560012 India |
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Abstract: | Ring-expansion strategies are valuable synthetic tools that take benefit of existing ring structures and evade the unfavorable enthalpic-and entropic effects that arise with end-to-end cyclizations. One potentially important class of such reactions is the Dowd–Beckwith reaction, the ring-expansion of ketones via alkoxy radicals. The exciting advancement in this research area is starting to show its potential, as demonstrated by applying this methodology in strategy-level bond formation to synthesize complex natural products. This Review aims to provide the first comprehensive survey of the development of the Dowd–Beckwith reaction spanning three decades from the initial report to the present day, thus providing the readers with great detail about the contributions of this reaction to organic synthesis. We hope that this review will further disclose the salient features of the Dowd–Beckwith reaction for synthetic applications and encourage the development of new, more advanced applications. |
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Keywords: | cascade Dowd–Beckwith reaction radical chemistry rearrangements total synthesis |
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