Total Synthesis of (+/-)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation
- Authors
- Tao, Eriko; Inoue, Masaki; Jeong, Taejoo; Kim, In Su; Yoshimitsu, Takehiko
- Issue Date
- Jul-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.85, no.14, pp 9064 - 9070
- Pages
- 7
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 85
- Number
- 14
- Start Page
- 9064
- End Page
- 9070
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/3835
- DOI
- 10.1021/acs.joc.0c00965
- ISSN
- 0022-3263
1520-6904
- Abstract
- A synthetic route to liphagal, a natural PI3K alpha inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.
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Collections - Pharmacy > Department of Pharmacy > 1. Journal Articles
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