Total Synthesis and Anticancer Activity of (+)-Hypercalin C and Congeners.

We report the first total synthesis of (+)-hypercalin C employing a convergent strategy that enabled dissection of the essential structural features required for the observed anticancer activity. A strategic disconnection involving an unusual Csp3-Csp2 Suzuki-Miyaura coupling with an α-bromo enolether also revealed an unexpected C-H activation. Our strategy targeted designed analogs along the synthetic route to address particular biological questions. Our results support the hypothesis that hypercalin C may act as a proton shuttle with the dearomatized acylphloroglucinol moiety being essential for this activity. PMID: 30600887 [PubMed - as supplied by publisher]
Source: Angewandte Chemie - Category: Chemistry Authors: Tags: Angew Chem Int Ed Engl Source Type: research