Synthetic study toward tridachiapyrone B.
2,5-cyclohexadienone
Robinson-type annulation
oxy-Cope
quaternary carbon
α’-methoxy-γ-pyrone
Journal
Beilstein journal of organic chemistry
ISSN: 1860-5397
Titre abrégé: Beilstein J Org Chem
Pays: Germany
ID NLM: 101250746
Informations de publication
Date de publication:
2022
2022
Historique:
received:
10
10
2022
accepted:
05
12
2022
entrez:
11
1
2023
pubmed:
12
1
2023
medline:
12
1
2023
Statut:
epublish
Résumé
A convergent approach to the skeleton of tridachiapyrone B is described taking advantage of the desymmetrization of α,α'-dimethoxy-γ-pyrone leading to α-crotyl-α'-methoxy-γ-pyrone in one step. To construct the quaternary carbon of the 2,5-cyclohexadienone of the target, a strategy based on the Robinson-type annulation of an aldehyde derived from α-crotyl-α'-methoxy-γ-pyrone was applied. The grafting of the simplified target's side chain was demonstrated through an oxidative anionic oxy-Cope rearrangement of the tertiary alcohol arising from the 1,2-addition of a 1,3-dimethylallyl reagent to 2,5-cyclohexadienone connected to the α'-methoxy-γ-pyrone motif.
Identifiants
pubmed: 36628263
doi: 10.3762/bjoc.18.183
pmc: PMC9795862
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1741-1748Informations de copyright
Copyright © 2022, Cormier et al.
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