Tandem Macrolactone Synthesis: Total Synthesis of (-)-Exiguolide by a Macrocyclization/Transannular Pyran Cyclization Strategy.
Macrolides
Natural Products
Tandem Reactions
Tetrahydropyrans
Transannular Reactions
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:
23 05 2022
23 05 2022
Historique:
received:
16
02
2022
pubmed:
5
3
2022
medline:
18
5
2022
entrez:
4
3
2022
Statut:
ppublish
Résumé
Tetrahydropyran-containing macrolactones were synthesized by integrating Meyer-Schuster rearrangement, macrocyclic ring-closing metathesis, and transannular oxa-Michael addition under gold and ruthenium catalysis. Single-step access to a variety of 14- to 20-membered macrolactones containing a tetrahydropyran ring was possible from readily available linear precursors in good yields and with moderate to excellent diastereoselectivity. A 13-step synthesis of (-)-exiguolide, an anticancer marine macrolide, showcased the feasibility of our tandem reaction sequence for macrolactone synthesis and also demonstrated the power of transannular reactions for rapid assembly of the tetrahydropyran rings of the target natural product.
Identifiants
pubmed: 35243740
doi: 10.1002/anie.202202549
doi:
Substances chimiques
Macrolides
0
Pyrans
0
exiguolide
0
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202202549Informations de copyright
© 2022 Wiley-VCH GmbH.
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