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Protecting-Group-Free Total Synthesis and Biological Evaluation of 3‑Methylkealiiquinone and Structural Analogues
The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A t...
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Published in: | Journal of organic chemistry 2018-09, Vol.83 (17), p.10627-10635 |
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Main Authors: | , , , |
Format: | Article |
Language: | English |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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Summary: | The modular protecting-group-free total synthesis of 3-methylkealiiquinone, an analogue of the marine alkaloid kealiiquinone, was accomplished in seven steps. A regioselectively constructed functionalized arylbenzimidazolone moiety and dimethyl squarate were used as the only two building blocks. A thermal ring expansion via 6π-conrotatory ring closure to build the quinone fragment gave rise to the desired linear analogue of the natural compound along with a nondescribed structurally attractive angular naphtho[1,2-d]imidazole regioisomer. The IC50 values for the compounds were determined on three cancer cell lines. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.8b01436 |