Citation: Tengfei Xuan, Xinyu Zhang, Wei Han, Yidong Huang, Weiwu Ren. Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B[J]. Chinese Chemical Letters, ;2025, 36(2): 109816. doi: 10.1016/j.cclet.2024.109816 shu

Total synthesis of (+)-taberdicatine B and (+)-tabernabovine B

Tengfei Xuan ^a ,
Xinyu Zhang ^a ,
Wei Han ^a ,
Yidong Huang ^a ,
Weiwu Ren ^{a, b, *,}

a.
Molecular Synthesis Center & Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
b.
Laboratory for Marine Drugs and Bioproducts, Laoshan Laboratory, Qingdao 266237, China

renweiwu@ouc.edu.cn

Received Date: 22 January 2024
Revised Date: 8 March 2024
Accepted Date: 22 March 2024
Available Online: 22 March 2024

Figures(4)

The first total synthesis of (+)-taberdicatine B and (+)-tabernabovine B has been accomplished in 10 steps with 26.9% overall yield and 15 steps with 7.3% overall yield, respectively. The prominent features of this efficient synthetic strategy include the following: (1) (+)-Taberdicatine B and (+)-tabernabovine B were accessed from common advanced intermediates by varying the substituents; (2) A one-pot asymmetric bromocyclization/hydrolysis was explored to assemble HPI skeleton; (3) Dieckmann condensation to form β-keto ester for the assembly of seven-membered ring; (4) An ester reduction/amide semireduction/cyclization sequence was applied to form the cage-like framework.
- Taberdicatine B,
- Tabernabovine B,
- Hexahydropyrrolo[2,3-b]indole,
- Asymmetric dearomatization,
- Total synthesis
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