An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5.
Diels-Alder reaction
ring-closing metathesis
terpenoids
total synthesis
transannular cycloaddition
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:
27 03 2020
27 03 2020
Historique:
received:
02
10
2019
revised:
04
11
2019
pubmed:
22
11
2019
medline:
22
11
2019
entrez:
22
11
2019
Statut:
ppublish
Résumé
We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. Ring-closing metathesis and an auxiliary-directed 1,4-addition are the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structural motif was established from a furanocembranoid through transannular [4+2] cycloaddition.
Identifiants
pubmed: 31750980
doi: 10.1002/anie.201912613
pmc: PMC7155007
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
5521-5525Informations de copyright
© 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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