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 inJournal of organic chemistry Vol. 83; no. 17; pp. 10627 - 10635
Main Authors Ramadoss, Velayudham, Alonso-Castro, Angel Josabad, Campos-Xolalpa, Nimsi, Solorio-Alvarado, César R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.09.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
AGENT
KEALIIQUINONE
REGIOSPECIFIC SYNTHESIS
DNA METHYLATION
QUINONES
7'-DESMETHYLKEALIIQUINONE
REARRANGEMENTS
MARINE NATURAL-PRODUCTS
CYCLOBUTENEDIONES
ALKALOIDS
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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