Synthesis of the A-F Fragment of the Pacific Ciguatoxin CTX3C by Iterative Ring-Closing Metathesis and Tsuji-Trost Allylation.
Tsuji-Trost allylation
ciguatoxin
iterative ring construction
polyether
ring-closing metathesis
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
22 Dec 2023
22 Dec 2023
Historique:
received:
09
10
2023
medline:
13
10
2023
pubmed:
13
10
2023
entrez:
13
10
2023
Statut:
ppublish
Résumé
The fully functionalized A-F fragment of the Pacific ciguatoxin CTX3C has been synthesized from a derivative of D-glucal, which serves as the B-ring. Rings A and C were introduced to either side of ring B by ring-closing diene and enyne metathesis (RCM). The seven-membered D-ring and eight-membered E-ring were assembled by iterative use of a six-step reaction sequence in which RCM was used for ring construction and Tsuji-Trost allylation was employed for subsequent stereoselective functionalization. The nine-membered F-ring was formed by use of an RCM reaction and bears the functionality required for attachment of the I-M fragment and subsequent closure of rings G and H.
Identifiants
pubmed: 37830907
doi: 10.1002/chem.202303121
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303121Subventions
Organisme : Engineering and Physical Sciences Research Council
ID : EP/R035423/1
Organisme : Engineering and Physical Sciences Research Council
ID : EP/K503058
Organisme : Engineering and Physical Sciences Research Council
ID : EP/L50497X
Organisme : Engineering and Physical Sciences Research Council
ID : EP/M506539
Organisme : Engineering and Physical Sciences Research Council
ID : EP/R513222/1
Organisme : Engineering and Physical Sciences Research Council
ID : EP/T517896/1
Informations de copyright
© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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