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One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling

The first total synthesis of (−)-huperzine W (1) has been achieved. Key element of the synthesis is a highly convergent assemblage for the two rings system of target molecule utilizing an efficient Suzuki-Miyaura coupling reaction between chiral iodide 2 and 2-allylpyrrolidinone 4. Evaluation of the...

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Detalles Bibliográficos
Autores principales: Xu, Tao, Jiang, Shi-Zhi, Luo, Huai-Rong, Yang, Yu-Rong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Berlin Heidelberg 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131606/
http://dx.doi.org/10.1007/s13659-012-0084-2
Descripción
Sumario:The first total synthesis of (−)-huperzine W (1) has been achieved. Key element of the synthesis is a highly convergent assemblage for the two rings system of target molecule utilizing an efficient Suzuki-Miyaura coupling reaction between chiral iodide 2 and 2-allylpyrrolidinone 4. Evaluation of the AchE inhibition of synthetic huperzine W was also carried out. [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: Supplementary material is available for this article at 10.1007/s13659-012-0084-2 and is accessible for authorized users.