Abstract
Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.
Original language | English |
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Pages (from-to) | 8998-9011 |
Journal | Organic and Biomolecular Chemistry |
Volume | 14 |
Issue number | 38 |
Early online date | 30 Aug 2016 |
DOIs | |
Publication status | Published - 14 Oct 2016 |