Chinese Journal of Organic Chemistry >
Synthetic Studies towards Streptoseomycin
Received date: 2024-10-13
Revised date: 2024-12-05
Online published: 2024-12-20
Supported by
Research Grants Council, University Grants Committee of Hong Kong(C6022-22W); Research Grants Council, University Grants Committee of Hong Kong(16300921); Research Grants Council, University Grants Committee of Hong Kong(16308922); Research Grants Council, University Grants Committee of Hong Kong(16304023)
Streptoseomycin belongs to the nargenicin family of macrolides with potent antibacterial activity. Due to the complex molecular structure, total synthesis of streptoseomycin has not been reported. Herein, our efforts on construction of the tricyclic core featuring ether-bridge across the cis-decalin with all requisite functionalities for streptoseomycin are reported. The key synthetic strategy relies on Diels-Alder reaction of benzoquinone with Danishefsky diene, intramolecular Michael addition, and intramolecular SN2 etherification. Our successful construction of this tricyclic core not only uncovered many unexpected transformations but also laid a solid ground for the total synthesis of streptoseomycin.
Key words： macrolide; decalin; Diels-Alder reaction; streptoseomycin
Ryungwoo Kim , Rongbiao Tong . Synthetic Studies towards Streptoseomycin[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 933 -944 . DOI: 10.6023/cjoc202409011
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