Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition
In this article, an efficient and straightforward protocol for the construction of complex dispirocyclic skeletons via regioselective intramolecular Michael addition is presented. Diverse dispirocyclic compounds were synthesized under mild and transition-metal-free conditions with good to excellent...
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| Format: | Article |
| Language: | English |
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MDPI AG
2025-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/15/3164 |
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| author | Weilun Cao Junmin Dong Xuan Pan Zhanzhu Liu |
| author_facet | Weilun Cao Junmin Dong Xuan Pan Zhanzhu Liu |
| author_sort | Weilun Cao |
| collection | DOAJ |
| description | In this article, an efficient and straightforward protocol for the construction of complex dispirocyclic skeletons via regioselective intramolecular Michael addition is presented. Diverse dispirocyclic compounds were synthesized under mild and transition-metal-free conditions with good to excellent yields. Most stereoisomers were conveniently separated by column chromatography, and their relative configurations were identified by single-crystal X-Ray diffraction of representative compounds. A scale-up experiment validated the practicality of this method. In an in vitro assay, some dispirocyclic compounds exhibited potent cytotoxicity with an IC<sub>50</sub> value of 10<sup>−6</sup> mol/L. |
| format | Article |
| id | doaj-art-5fefbb911b3b4ae992ad04e311a0c3b8 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-5fefbb911b3b4ae992ad04e311a0c3b82025-08-20T03:02:49ZengMDPI AGMolecules1420-30492025-07-013015316410.3390/molecules30153164Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael AdditionWeilun Cao0Junmin Dong1Xuan Pan2Zhanzhu Liu3State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, ChinaState Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, ChinaState Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, ChinaState Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, ChinaIn this article, an efficient and straightforward protocol for the construction of complex dispirocyclic skeletons via regioselective intramolecular Michael addition is presented. Diverse dispirocyclic compounds were synthesized under mild and transition-metal-free conditions with good to excellent yields. Most stereoisomers were conveniently separated by column chromatography, and their relative configurations were identified by single-crystal X-Ray diffraction of representative compounds. A scale-up experiment validated the practicality of this method. In an in vitro assay, some dispirocyclic compounds exhibited potent cytotoxicity with an IC<sub>50</sub> value of 10<sup>−6</sup> mol/L.https://www.mdpi.com/1420-3049/30/15/3164spiro compoundsregioselectivitytransition-metal free |
| spellingShingle | Weilun Cao Junmin Dong Xuan Pan Zhanzhu Liu Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition Molecules spiro compounds regioselectivity transition-metal free |
| title | Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition |
| title_full | Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition |
| title_fullStr | Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition |
| title_full_unstemmed | Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition |
| title_short | Straightforward Access to the Dispirocyclic Framework via Regioselective Intramolecular Michael Addition |
| title_sort | straightforward access to the dispirocyclic framework via regioselective intramolecular michael addition |
| topic | spiro compounds regioselectivity transition-metal free |
| url | https://www.mdpi.com/1420-3049/30/15/3164 |
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