Total Synthesis of the Diterpene Waihoensene.
Pauson-Khand reaction
natural products
radicals
terpenes
total synthesis
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
08 02 2021
08 02 2021
Historique:
received:
18
08
2020
pubmed:
27
10
2020
medline:
27
10
2020
entrez:
26
10
2020
Statut:
ppublish
Résumé
A racemic and scalable enantioselective total synthesis of (+)-waihoensene was accomplished. (+)-Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all-cis-fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson-Khand reaction, a diastereoselective α-alkylation, and a diastereoselective 1,4-addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale.
Identifiants
pubmed: 33103334
doi: 10.1002/anie.202011298
pmc: PMC7898921
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
2939-2942Informations de copyright
© 2020 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.
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