Metal-free synthesis of dihydrofuran derivatives as anti-vicinal amino alcohol isosteres
- Authors
- Nangunuri, Bhargav Gupta; Shirke, Rajendra P. P.; Kim, Mi-hyun
- Issue Date
- Feb-2023
- Publisher
- ROYAL SOC CHEMISTRY
- Citation
- ORGANIC & BIOMOLECULAR CHEMISTRY, v.21, no.5, pp.960 - 965
- Journal Title
- ORGANIC & BIOMOLECULAR CHEMISTRY
- Volume
- 21
- Number
- 5
- Start Page
- 960
- End Page
- 965
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/86889
- DOI
- 10.1039/d2ob02077g
- ISSN
- 1477-0520
- Abstract
- Dihydrofuran cores are commonly incorporated into synthetically and pharmacologically significant scaffolds in natural product and drug discovery chemistry. Herein, we report a concise and practical strategy to construct spiro-dihydrofuran and amino dihydrofuran scaffolds as anti-vicinal amino alcohol isosteres. Hypervalent iodine (PhI(OAc)(NTs2))-mediated C-H activation of alkynes resulted in two-bond formations with one pi bond cleavage: (i) C(sp(2))-N(sp(3)) and O(sp(3))-C(sp(2)); (ii) C(sp(2))-N(sp(3)) and C(sp(3))-C(sp(2)). The metal-free 5-endo-dig oxidative cyclization provided versatile amino 2,3- and 2,5-dihydrofurans bearing the C-5 quaternary carbon. The non-toxicity of all synthesised dihydrofurans was verified via in vitro cell viability assay.
- Files in This Item
- There are no files associated with this item.
- Appears in
Collections - 약학대학 > 약학과 > 1. Journal Articles
![qrcode](https://api.qrserver.com/v1/create-qr-code/?size=55x55&data=https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/86889)
Items in ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.