An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies
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 configura...
| Main Authors: | , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.19 |
| _version_ | 1811158702198095872 |
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| author | Tharun K. Kotammagari Sweta Misra Sayantan Paul Sunita Kunte Rajesh G. Gonnade Manas K. Santra Asish K. Bhattacharya |
| author_facet | Tharun K. Kotammagari Sweta Misra Sayantan Paul Sunita Kunte Rajesh G. Gonnade Manas K. Santra Asish K. Bhattacharya |
| author_sort | Tharun K. Kotammagari |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-10T05:27:31Z |
| format | Article |
| id | doaj.art-fd5c7a08e0004b18b5e458313a587f53 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-04-10T05:27:31Z |
| publishDate | 2023-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-fd5c7a08e0004b18b5e458313a587f532023-03-07T13:31:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-02-0119120421110.3762/bjoc.19.191860-5397-19-19An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studiesTharun K. Kotammagari0Sweta Misra1Sayantan Paul2Sunita Kunte3Rajesh G. Gonnade4Manas K. Santra5Asish K. Bhattacharya6Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India Cancer Biology Division, National Centre for Cell Sciences, Ganesh Khind Road, Pune-411 007, India Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India Centre for Material Characterization, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India Cancer Biology Division, National Centre for Cell Sciences, Ganesh Khind Road, Pune-411 007, India Division of Organic Chemistry, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune-411 008, India 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.https://doi.org/10.3762/bjoc.19.19dimerizationincarviditoneincarvilleatoneoxa-michaelrauhut–currier |
| spellingShingle | Tharun K. Kotammagari Sweta Misra Sayantan Paul Sunita Kunte Rajesh G. Gonnade Manas K. Santra Asish K. Bhattacharya An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies Beilstein Journal of Organic Chemistry dimerization incarviditone incarvilleatone oxa-michael rauhut–currier |
| title | An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies |
| title_full | An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies |
| title_fullStr | An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies |
| title_full_unstemmed | An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies |
| title_short | An accelerated Rauhut–Currier dimerization enabled the synthesis of (±)-incarvilleatone and anticancer studies |
| title_sort | accelerated rauhut currier dimerization enabled the synthesis of incarvilleatone and anticancer studies |
| topic | dimerization incarviditone incarvilleatone oxa-michael rauhut–currier |
| url | https://doi.org/10.3762/bjoc.19.19 |
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