Enantioselective total synthesis of altersolanol A and N.
Asymmetric synthesis
Diels-Alder reaction
Enantioselectivity
Natural product
Journal
Bioorganic & medicinal chemistry
ISSN: 1464-3391
Titre abrégé: Bioorg Med Chem
Pays: England
ID NLM: 9413298
Informations de publication
Date de publication:
01 07 2019
01 07 2019
Historique:
received:
26
03
2019
accepted:
26
04
2019
pubmed:
11
5
2019
medline:
2
9
2020
entrez:
11
5
2019
Statut:
ppublish
Résumé
The development of the first enantioselective total synthesis of altersolanol N is reported. The decisive step of the synthesis is the enantioselective formation of the tetrahydroanthraquinone nucleus by a [4 + 2]-cycloaddition in high yield and with excellent diastereo- and enantioselectivity (>95:5 dr and 95:5 er). In addition, a demanding selective monoacetylation of the OH group at the C-2 position was achieved: an epoxide ring opening with the participation of a neighbouring acetyl group could be established. The route proved to be an efficient alternative to also access enantiomerically pure altersolanol A.
Identifiants
pubmed: 31072649
pii: S0968-0896(19)30489-4
doi: 10.1016/j.bmc.2019.04.033
pii:
doi:
Substances chimiques
Anthraquinones
0
altersolanol A
22268-16-2
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2991-2997Informations de copyright
Copyright © 2019 Elsevier Ltd. All rights reserved.