Total Syntheses of (-)-Conidiogenone B, (-)-Conidiogenone, and (-)-Conidiogenol.
Danheiser annulation
Nicholas/Pauson--Khand reaction
cyclopianes
diterpenes
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:
14 09 2020
14 09 2020
Historique:
received:
19
05
2020
pubmed:
6
6
2020
medline:
6
6
2020
entrez:
6
6
2020
Statut:
ppublish
Résumé
Cyclopianes are novel diterpenes featuring a highly strained 6/5/5/5 tetracyclic core embedded with 6-8 consecutive stereocenters. The concise total syntheses of (-)-conidiogenone B, (-)-conidiogenone, and (-)-conidiogenol have been accomplished in 14-17 steps. The present work features a HAT-mediated alkene-nitrile cyclization to access the cis-biquinane, a Nicholas/Pauson-Khand reaction to construct the linear triquinane, and a Danheiser annulation to afford the congested angular triquinane skeleton.
Identifiants
pubmed: 32502325
doi: 10.1002/anie.202007247
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
16475-16479Informations de copyright
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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