Efficient Synthesis of 1-Thiomansonones with Anti-MRSA Activity

^◊ S.-H. Park and S. Park contributed equally to this work.

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.

Key words

Newman–Kwart - mansonones - palladium - orthoquinones - thiaphenalene - MRSA

• References and Notes

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