Synthetic Studies towards Streptoseomycin

doi:10.6023/cjoc202409011

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (3): 933-944.DOI: 10.6023/cjoc202409011 Previous Articles Next Articles

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汉城链霉素的合成研究

金令愚, 童荣标^*()

香港科技大学化学系香港九龙 999077

收稿日期:2024-10-13 修回日期:2024-12-05 发布日期:2024-12-19
基金资助:
大学教育资助委员会-研资局(香港)(C6022-22W); 大学教育资助委员会-研资局(香港)(16300921); 大学教育资助委员会-研资局(香港)(16308922); 大学教育资助委员会-研资局(香港)(16304023)

Synthetic Studies towards Streptoseomycin

Ryungwoo Kim, Rongbiao Tong()

Department of Chemistry, The Hong Kong University of Science and Technology, Kowloon, Hong Kong 999077

Received:2024-10-13 Revised:2024-12-05 Published:2024-12-19
Contact: * E-mail: rtong@ust.hk
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)

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Abstract

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 S_N2 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

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Ryungwoo Kim, Rongbiao Tong. Synthetic Studies towards Streptoseomycin[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 933-944.

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Fig. & Tab. 4

Figure 1. Representative members of nargenicin macrolides

Scheme 1. Retrosynthetic analysis of streptoseomycin

Scheme 2. Synthesis of fully functionalized cis-decalin

Scheme 3. Synthesis of fully functionalized tricyclic core with oxa-bridge across cis-decalin

References 45

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汉城链霉素的合成研究

Synthetic Studies towards Streptoseomycin

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