Citation: Xuan Pan, Tao Sheng, Zhanzhu Liu. A concise total synthesis of monoterpenoid indole alkaloid (-)-voacafricine A[J]. Chinese Chemical Letters, ;2025, 36(10): 110913. doi: 10.1016/j.cclet.2025.110913 shu

A concise total synthesis of monoterpenoid indole alkaloid (-)-voacafricine A

State Key Laboratory of Bioactive Substances and Functions of Natural Medicines, Institute of Materia Medica, Peking Union Medical College and Chinese Academy of Medical Sciences, Beijing 100050, China

liuzhanzhu@imm.ac.cn

Received Date: 29 October 2024
Revised Date: 14 January 2025
Accepted Date: 3 February 2025
Available Online: 4 February 2025

Figures(9)

A concise total synthesis of novel monoterpenoid indole alkaloid (-)-voacafricine A is described, which proceeded in 14 longest linear steps and 5.2% overall yield. Key transformations comprised of (a) an organocatalytically asymmetric Pictet-Spengler cyclization/lactamization cascade reaction generating the key tetracyclic lactam skeleton; (b) asymmetric α-alkylation of carbonyl group induced by Evans' chiral auxiliary with excellent diastereoselectivity; (c) a highly efficient one-pot desulfurization/hydrogenation/debenzylation transformation using Raney Ni under hydrogen atmosphere; as well as (d) an intramolecular Vorbürggen reaction constructing the quaternary ammonium motif and the final cagelike skeleton.
- (-)-Voacafricine A,
- Pictet-Spengler cyclization,
- Evans' chiral auxiliary,
- Lawesson's reagent,
- Vorbürggen reaction
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