Citation: Qunlong Zhang, Jingyi Kang, Jingwen Wang, Tiancheng Tan, Zhaoyong Lu. Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G[J]. Chinese Chemical Letters, ;2025, 36(3): 109915. doi: 10.1016/j.cclet.2024.109915 shu

Divergent total synthesis of sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G

Qunlong Zhang ^a ,
Jingyi Kang ^a ,
Jingwen Wang ^a ,
Tiancheng Tan ^a ,
Zhaoyong Lu ^{a, b, *,}

a.
State Key Laboratory of Medicinal Chemical Biology, College of Pharmacy, Nankai University, Tianjin 300350, China
b.
Nankai International Advanced Research Institute (Shenzhen Futian), Nankai University, Shenzhen 518045, China

Received Date: 28 February 2024
Revised Date: 12 April 2024
Accepted Date: 21 April 2024
Available Online: 24 April 2024

Figures(6)

The first total synthesis of marine sesquiterpene (hydro)quinone meroterpenoids dysideanones A and E–G (1 and 4–6) has been accomplished in an enantioselective and divergent way. The sesquiterpene fragment and the aromatic moiety were efficiently connected via a site-selective and diastereoselective intermolecular alkylation of Wieland–Miescher ketone derivative 9 and benzyl bromide 10. The core 6/6/6/6-fused backbone of dysideanones was efficiently constructed through an intramolecular radical cyclization reaction. Dysideanone G (6) was easily prepared on a gram-scale and dysideanones A, E, and F (1, 4, and 5) were divergently transformed from dysideanone G (6) in one or two steps
- Marine natural product,
- Sesquiterpene (hydro)quinone,
- Meroterpenoid,
- Total synthesis,
- Dysideanone
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沈阳化工大学材料科学与工程学院沈阳 110142