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...

Descripción completa

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:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131606/
http://dx.doi.org/10.1007/s13659-012-0084-2
_version_ 1782330491189329920
author Xu, Tao
Jiang, Shi-Zhi
Luo, Huai-Rong
Yang, Yu-Rong
author_facet Xu, Tao
Jiang, Shi-Zhi
Luo, Huai-Rong
Yang, Yu-Rong
author_sort Xu, Tao
collection PubMed
description 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.
format Online
Article
Text
id pubmed-4131606
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Springer Berlin Heidelberg
record_format MEDLINE/PubMed
spelling pubmed-41316062014-08-20 One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling Xu, Tao Jiang, Shi-Zhi Luo, Huai-Rong Yang, Yu-Rong Nat Prod Bioprospect Short Communication 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. Springer Berlin Heidelberg 2012-12-14 /pmc/articles/PMC4131606/ http://dx.doi.org/10.1007/s13659-012-0084-2 Text en © The Author(s) 2012 https://creativecommons.org/licenses/by/4.0/This article is published under license to BioMed Central Ltd. Open Access This article is distributed under the terms of the Creative Commons Attribution License which permits any use, distribution, and reproduction in any medium, provided the original author(s) and source are credited.
spellingShingle Short Communication
Xu, Tao
Jiang, Shi-Zhi
Luo, Huai-Rong
Yang, Yu-Rong
One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title_full One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title_fullStr One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title_full_unstemmed One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title_short One-step synthesis of Lycopodium alkaloid (-)-huperzine W via Suzuki-Miyaura coupling
title_sort one-step synthesis of lycopodium alkaloid (-)-huperzine w via suzuki-miyaura coupling
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4131606/
http://dx.doi.org/10.1007/s13659-012-0084-2
work_keys_str_mv AT xutao onestepsynthesisoflycopodiumalkaloidhuperzinewviasuzukimiyauracoupling
AT jiangshizhi onestepsynthesisoflycopodiumalkaloidhuperzinewviasuzukimiyauracoupling
AT luohuairong onestepsynthesisoflycopodiumalkaloidhuperzinewviasuzukimiyauracoupling
AT yangyurong onestepsynthesisoflycopodiumalkaloidhuperzinewviasuzukimiyauracoupling

Ejemplares similares