| Autor: |
Qing-Hua Li, Dingding Gao, Cheng-Yu He, Qi Liao, Yun-Xuan Tan, Yu-Hui Wang, Rui Ding, Guo-Qiang Lin, Ping Tian |
| Jazyk: |
angličtina |
| Rok vydání: |
2020 |
| Předmět: |
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| Zdroj: |
Cell Reports Physical Science, Vol 1, Iss 10, Pp 100222- (2020) |
| Druh dokumentu: |
article |
| ISSN: |
2666-3864 |
| DOI: |
10.1016/j.xcrp.2020.100222 |
| Popis: |
Summary: Bridged and fused polycyclic structures are found in a huge number of natural products. Significant progress has been made on their syntheses; however, facile and practical strategies to afford polycycles with tunable substituents and functional groups remain rare. Here, we report a practical rhodium(III)-catalyzed asymmetric borylative cyclization of cyclohexadienone-containing 1,6-enynes, affording highly enantioenriched cis-bicyclic frameworks with great functional group compatibility, and further extend it to construct bridged tricyclic and fused tetracyclic skeletons in one-pot protocols. The combination of borylative cyclization with a subsequent oxidation/aldol reaction sequence goes through an epimerization of the stereocenter adjacent to the acetyl group, yielding various tricyclic compounds. In addition, borylative cyclization is combined with a Suzuki-Miyaura coupling/Michael addition sequence, leading to diverse tetracyclic compounds. Starting from simple starting materials, both one-pot transformations yield complex products bearing several consecutive stereocenters with excellent enantioselectivities. Furthermore, an unnatural steroid-like compound is also readily prepared, demonstrating the potential of this methodology. |
| Databáze: |
Directory of Open Access Journals |
| Externí odkaz: |
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