Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 5, Pages 563-580Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1316850
Keywords
benzocyclobutenones; cycloaddition; C-C bond cleavage; o-quinone dimethides; fused pi-aromatic systems; ring expansion
Categories
Funding
- ICIQ Foundation
- European Research Council [ERC-277883]
- MICINN [CTQ2009-13840, CTQ2012-34054]
- MICINN
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Benzocyclobutenones are an intriguing class of four-membered-ring ketones that have been used extensively as powerful synthetic intermediates in organic synthesis. Their high reactivity is primarily attributed to the unique high electrophilicity of the carbonyl unit and the ability to generate o-quinone dimethides, allowing a myriad of different transformations. However, the synthesis of benzocyclobutenones still represents a great challenge. This review provides an overview of the preparation, use and impact of benzocyclobutenones in organic synthesis. Selected applications in the synthesis of natural products are also described, in order to illustrate the utility of these compounds.
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