AI Article Synopsis
- Hypercalins are compounds with unique chemical structures that have shown potential against various cancer cell lines, specifically with hypercalin C being a focus of research.
- The first total synthesis of (+)-hypercalin C was achieved using a convergent strategy, which allowed researchers to analyze the key structural components linked to its anticancer effects.
- Innovative techniques, including a distinct C-C coupling method and C-H activation, were utilized in the synthesis process to explore analogues and uncover hypercalin C’s possible role as a proton shuttle in its bioactivity.
Article Abstract
The hypercalins are dearomatized acylphloroglucinols with a pendant complex cyclopentane ring that exhibit activity against several cancer cell lines. We report the first total synthesis of (+)-hypercalin C employing a convergent strategy that enabled the dissection of the essential structural features required for the observed anticancer activity. A strategic disconnection involving an unusual C -C Suzuki-Miyaura coupling with an α-bromo enolether also revealed an unexpected C-H activation. This strategy targeted designed analogues along the synthetic route to address particular biological questions. These results support the hypothesis that hypercalin C may act as a proton shuttle with the dearomatized acylphloroglucinol moiety being essential for this activity.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6438696 | PMC |
| http://dx.doi.org/10.1002/anie.201812909 | DOI Listing |
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