An Approach towards the Synthesis of the Spiroimine Fragment of 13-Desmethylspirolide C and Gymnodimine A.
Diels-Alder reaction
asymmetric synthesis
natural products
quaternary stereocenters
spiroimine
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
A general access to the spiroimine skeleton of gymnodimine and spirolides is described, relying on the construction of the cyclohexene fragment using an enantiocontrolled Diels-Alder reaction, the installation of the all-carbon quaternary stereocenter through a stereocontrolled alkylation or aldolisation and the elaboration of the lateral chains at C7 and C22 using Wittig-Horner olefinations. The spiroimine core of gymnodimine is made available through a 16-step linear sequence in a 21 % overall yield.
Identifiants
pubmed: 30358921
doi: 10.1002/chem.201804972
doi:
Types de publication
Journal Article
Langues
eng
Pagination
1553-1560Subventions
Organisme : Agence Nationale de la Recherche
ID : 11-BS07-006-02
Organisme : Région Aquitaine
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.