Synthesis of dihydrotropone derivatives using an anionic 8π-electrocyclic reaction

A new method to synthesise functionalised cycloheptatrienes was established using the anionic 8π-electrocyclic reaction of β-ketoester-derived dienyne substrates. The cyclised products were converted to a variety of cycloheptatriene derivatives including tropones. Using this method, a concise, first...

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Published inChemical communications (Cambridge, England) Vol. 6; no. 52; pp. 6619 - 6622
Main Authors Kato, Ranmaru, Suzuki, Takahiro, Tanino, Keiji
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 25.06.2024
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
Substrates
Synthesis
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Summary:A new method to synthesise functionalised cycloheptatrienes was established using the anionic 8π-electrocyclic reaction of β-ketoester-derived dienyne substrates. The cyclised products were converted to a variety of cycloheptatriene derivatives including tropones. Using this method, a concise, first total synthesis of (−)-orobanone, a natural sesquiterpenoid, was achieved. A new method to synthesise functionalised cycloheptatrienes was established using the anionic 8π-electrocyclic reaction of β-ketoester-derived dienyne substrates.
Bibliography:Electronic supplementary information (ESI) available: Supporting materials, experimental procedures, and NMR spectra. See DOI
https://doi.org/10.1039/d4cc02273d
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc02273d