Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B
Abstract Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor thro...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55560-9 |
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| author | Yunxia Yang Dong Xie Liang Huo Yue Liu Jinbo Duan Huilin Li Pan-Pan Zhou Xingang Xie Xuegong She |
| author_facet | Yunxia Yang Dong Xie Liang Huo Yue Liu Jinbo Duan Huilin Li Pan-Pan Zhou Xingang Xie Xuegong She |
| author_sort | Yunxia Yang |
| collection | DOAJ |
| description | Abstract Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature. |
| format | Article |
| id | doaj-art-fbe01b0c0b1c413aae05f2e1200294ab |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-fbe01b0c0b1c413aae05f2e1200294ab2025-01-05T12:39:41ZengNature PortfolioNature Communications2041-17232025-01-011611910.1038/s41467-024-55560-9Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and BYunxia Yang0Dong Xie1Liang Huo2Yue Liu3Jinbo Duan4Huilin Li5Pan-Pan Zhou6Xingang Xie7Xuegong She8State 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 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 Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction. This synthesis establishes a concise asymmetric approach to access artatrovirenols A and B, and also provides insightful evidence to their biogenetic pathway in nature.https://doi.org/10.1038/s41467-024-55560-9 |
| spellingShingle | Yunxia Yang Dong Xie Liang Huo Yue Liu Jinbo Duan Huilin Li Pan-Pan Zhou Xingang Xie Xuegong She Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B Nature Communications |
| title | Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B |
| title_full | Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B |
| title_fullStr | Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B |
| title_full_unstemmed | Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B |
| title_short | Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B |
| title_sort | bioinspired concise synthesis of caged sesquiterpenoids artatrovirenols a and b |
| url | https://doi.org/10.1038/s41467-024-55560-9 |
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