An accelerated Rauhut-Currier dimerization enabled synthesis of (±)-Incarvilleatone and anticancer studies

Submitting author affiliation:
CSIR-National Chemical Laboratory, Pune, India

Beilstein Arch. 2022, 202287.

Published 16 Nov 2022

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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, one-pot synthesis of (±)-incarviditone has been achieved from rac-rengyolone by using KHMDS as a base. We have also assessed the anti-cancer activity of all the synthesized compounds in breast cancer cells nonetheless, they exhibited very limited growth suppression activity.

Keywords: oxa-Michael • Rauhut-Currier • dimerization • incarvilleatone • incarviditone

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Kotammagari, T. K.; Misra, S.; Paul, S.; Kunte, S.; Gonnade, R. G.; Santra, M. K.; Bhattacharya, A. K. Beilstein Arch. 2022, 202287. doi:10.3762/bxiv.2022.87.v1

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