Total Synthesis and Anticancer Activity of (+)-Hypercalinâ
C and Congeners.
Angew Chem Int Ed Engl
; 58(9): 2734-2738, 2019 02 25.
Article
em En
| MEDLINE
| ID: mdl-30600887
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 sp3 -C sp2 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 hypercalinâ
C may act as a proton shuttle with the dearomatized acylphloroglucinol moiety being essential for this activity.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Ciclopentanos
/
Antineoplásicos
Limite:
Humans
Idioma:
En
Ano de publicação:
2019
Tipo de documento:
Article