An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies

Autor: Tharun K. Kotammagari, Sweta Misra, Sayantan Paul, Sunita Kunte, Rajesh G. Gonnade, Manas K. Santra, Asish K. Bhattacharya
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 19, Iss 1, Pp 204-211 (2023)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.19.19
Popis: The total synthesis of racemic incarvilleatone has been achieved by utilizing unexplored accelerated Rauhut–Currier (RC) dimerization. The other key steps of the synthesis are oxa-Michael and aldol reactions in a tandem sequence. Racemic incarvilleatone was separated by chiral HPLC and the configuration of each enantiomer was determined by single-crystal X-ray analysis. In addition, a one-pot synthesis of (±)-incarviditone has been achieved from rac-rengyolone by using KHMDS as a base. We have also assessed the anticancer activity of all the synthesized compounds in breast cancer cells nonetheless, they exhibited very limited growth suppression activity.
Databáze: Directory of Open Access Journals