Efficient Synthesis of 1-Thiomansonones with Anti-MRSA Activity

Abstract In this study, we developed an efficient and general synthetic strategy for thiaphenalene, a sulfur-containing polyaromatic hetero­cycle, and applied for the synthesis of 1-thio derivatives of mansonone I and F, natural 1-oxaphenalenic orthoquinones. The pivotal steps for the construction o...

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Bibliographic Details
Published in:Synlett 2018-04, Vol.29 (7), p.938-942
Main Authors: Park, Seong-Hyuk, Park, Sooyoung, Lee, Chang-Yong, Suh, Young-Ger, Shin, Dongyun
Format: Article
Language:English
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Summary:Abstract In this study, we developed an efficient and general synthetic strategy for thiaphenalene, a sulfur-containing polyaromatic hetero­cycle, 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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1591894