Synthetic Studies on Spirolides A and B: Formation of the Upper Carbon Framework Based on a Lewis Acid Template-Catalyzed Diels-Alder Reaction.
Diels-Alder reaction
Lewis acids
catalytic reaction
natural products
spiro compounds
stereoselective reactions
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
28 Jan 2019
28 Jan 2019
Historique:
received:
01
10
2018
pubmed:
26
10
2018
medline:
26
10
2018
entrez:
26
10
2018
Statut:
ppublish
Résumé
The upper fragment of spirolides A and B, which are marine phycotoxins that exhibit strong antagonistic activities on nicotinic acetylcholine receptors, was constructed. The functionalized cyclohexene in spirolides was stereoselectively synthesized from the bicyclic lactone, which could be readily accessed by the Lewis acid template-catalyzed asymmetric Diels-Alder reaction of the pentadienol and methyl acrylate.
Identifiants
pubmed: 30357942
doi: 10.1002/chem.201804977
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1543-1552Subventions
Organisme : Japan Society for the Promotion of Science London
ID : 21590012
Organisme : the Japan Society for the Promotion of Science (JSPS)
ID : 15K07861
Organisme : the Japan Society for the Promotion of Science (JSPS)
ID : 16H05074
Organisme : the Japan Society for the Promotion of Science (JSPS)
ID : 21590012
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.