Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone
Abstract Electronically mismatched Diels−Alder reaction between two electron-deficient components is synthetically useful and yet underdeveloped under thermal conditions. Herein, a photoinduced formal [4 + 2] cycloaddition of enone with a variety of electron-deficient dienes is described. Key to the...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-11-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-54117-0 |
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| _version_ | 1846165114654294016 |
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| author | Zhezhe Xu Weibo Peng Jiarui Huang Jinhui Shen Jing-Jing Guo Anhua Hu |
| author_facet | Zhezhe Xu Weibo Peng Jiarui Huang Jinhui Shen Jing-Jing Guo Anhua Hu |
| author_sort | Zhezhe Xu |
| collection | DOAJ |
| description | Abstract Electronically mismatched Diels−Alder reaction between two electron-deficient components is synthetically useful and yet underdeveloped under thermal conditions. Herein, a photoinduced formal [4 + 2] cycloaddition of enone with a variety of electron-deficient dienes is described. Key to the success of this stepwise methodology relies on a C − C bond cleavage/rearrangement of the cyclobutane based overbred intermediate via diversified mechanistic pathways. Based on this annulation method, total synthesis of lucidumone is achieved in nine steps. |
| format | Article |
| id | doaj-art-53785540507a4e39b466fc4855e77cb7 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-53785540507a4e39b466fc4855e77cb72024-11-17T12:34:58ZengNature PortfolioNature Communications2041-17232024-11-011511710.1038/s41467-024-54117-0Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumoneZhezhe Xu0Weibo Peng1Jiarui Huang2Jinhui Shen3Jing-Jing Guo4Anhua Hu5State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou UniversityAbstract Electronically mismatched Diels−Alder reaction between two electron-deficient components is synthetically useful and yet underdeveloped under thermal conditions. Herein, a photoinduced formal [4 + 2] cycloaddition of enone with a variety of electron-deficient dienes is described. Key to the success of this stepwise methodology relies on a C − C bond cleavage/rearrangement of the cyclobutane based overbred intermediate via diversified mechanistic pathways. Based on this annulation method, total synthesis of lucidumone is achieved in nine steps.https://doi.org/10.1038/s41467-024-54117-0 |
| spellingShingle | Zhezhe Xu Weibo Peng Jiarui Huang Jinhui Shen Jing-Jing Guo Anhua Hu Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone Nature Communications |
| title | Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone |
| title_full | Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone |
| title_fullStr | Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone |
| title_full_unstemmed | Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone |
| title_short | Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone |
| title_sort | photoinduced formal 4 2 cycloaddition of two electron deficient olefins and its application to the synthesis of lucidumone |
| url | https://doi.org/10.1038/s41467-024-54117-0 |
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