| Title | Asymmetric Synthesis of the epi-Vinigrol Tricyclic Core Enabled by a Wolff Rearrangement Strategy and Formal Total Synthesis of (-)-Vinigrol |
| Author | |
| Corresponding Author | Min, Long; Li, Chuang-Chuang |
| Publication Years | 2023-10-11
|
| DOI | |
| Source Title | |
| ISSN | 0022-3263
|
| EISSN | 1520-6904
|
| Volume | 88Issue:20 |
| Abstract | A new approach to construct the tricyclic framework of the diterpenoid vinigrol is described. The challenging 1,5-butanodecahydronaphthalene core was established efficiently and diastereoselectively through a combination of type II [5 + 2] cycloaddition and Wolff rearrangement. In addition, a formal total synthesis of (-)-vinigrol was achieved in 12 steps, in which Baran's intermediate was efficiently produced from a known compound by a two-step sequence involving a stereoselective alpha-hydroxylation and a diastereoselective alpha-ketol rearrangement. |
| URL | [Source Record] |
| Indexed By | |
| Language | English
|
| SUSTech Authorship | First
; Corresponding
|
| Funding Project | National Natural Science Foundation of China["22271137","22225102"]
; National Key R& D Program of China[2022YFE0205500]
; Department of Science and Technology of Guangdong Province[2021A1515010164]
; Shenzhen Bay Laboratory[SZBL2021080601005]
; Shenzhen Science and Technology Innovation Committee["JCYJ20220818100603008","JCYJ20210324104408023"]
|
| WOS Research Area | Chemistry
|
| WOS Subject | Chemistry, Organic
|
| WOS Accession No | WOS:001089440600001
|
| Publisher | |
| ESI Research Field | CHEMISTRY
|
| Data Source | Web of Science
|
| Citation statistics | |
| Document Type | Journal Article |
| Identifier | http://kc.sustech.edu.cn/handle/2SGJ60CL/582774 |
| Department | Department of Chemistry 深圳格拉布斯研究院 |
| Affiliation | 1.Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Peoples R China 2.Shenzhen Bay Lab, Shenzhen 518132, Peoples R China |
| First Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| Corresponding Author Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| First Author's First Affilication | Department of Chemistry; Shenzhen Grubbs Institute |
| Recommended Citation GB/T 7714 |
Lin, Xiaohong,Min, Long,Li, Chuang-Chuang. Asymmetric Synthesis of the epi-Vinigrol Tricyclic Core Enabled by a Wolff Rearrangement Strategy and Formal Total Synthesis of (-)-Vinigrol[J]. JOURNAL OF ORGANIC CHEMISTRY,2023,88(20).
|
| APA |
Lin, Xiaohong,Min, Long,&Li, Chuang-Chuang.(2023).Asymmetric Synthesis of the epi-Vinigrol Tricyclic Core Enabled by a Wolff Rearrangement Strategy and Formal Total Synthesis of (-)-Vinigrol.JOURNAL OF ORGANIC CHEMISTRY,88(20).
|
| MLA |
Lin, Xiaohong,et al."Asymmetric Synthesis of the epi-Vinigrol Tricyclic Core Enabled by a Wolff Rearrangement Strategy and Formal Total Synthesis of (-)-Vinigrol".JOURNAL OF ORGANIC CHEMISTRY 88.20(2023).
|
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