Efficient Synthesis of 1-Thiomansonones with Anti-MRSA Activity
- Authors
- Park, Seong-Hyuk; Park, Sooyoung; Lee, Chang-Yong; Suh, Young-Ger; Shin, Dongyun
- Issue Date
- Apr-2018
- Publisher
- GEORG THIEME VERLAG KG
- Keywords
- Newman-Kwart; mansonones; palladium; orthoquinones; thiaphenalene; MRSA
- Citation
- SYNLETT, v.29, no.7, pp.938 - 942
- Journal Title
- SYNLETT
- Volume
- 29
- Number
- 7
- Start Page
- 938
- End Page
- 942
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/3895
- DOI
- 10.1055/s-0036-1591894
- ISSN
- 0936-5214
- Abstract
- In this study, we developed an efficient and general synthetic strategy for thiaphenalene, a sulfur-containing polyaromatic hetero-cycle, and applied for the synthesis of 1-thio derivatives of mansonone I and F, natural 1-oxaphenalenic orthoquinones. The pivotal steps for the construction of thiophenalene skeleton include formation of arylsulfide by Newman-Kwart rearrangement of thiocarbamate or palladium-catalyzed cross-coupling, and pericyclic ring closure. Three bioisosterically modified orthoquinones were synthesized and were evaluated for anti-MRSA activity.
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