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Occurrence, synthesis and applications of natural and designed [3.3.3]propellanes

Dilmaç, Alicia M. 1; Wezeman, Tim 1; Bär, Robin M. 1; Bräse, Stefan 1,2
1 Institut für Organische Chemie (IOC), Karlsruher Institut für Technologie (KIT)
2 Institut für Toxikologie und Genetik (ITG), Karlsruher Institut für Technologie (KIT)


The synthetically challenging [3.3.3]propellane core has caught a lot of attention over the last 50 years. This comprehensive review details all synthetic strategies reported in the period 1978–2019 to facilitate the synthesis of carbocyclic [3.3.3]propellanes. The described strategies span from acid-catalyzed rearrangements and photo-mediated cycloadditions of ketones, heteropropellanes and dispiroundecanes to thermal rearrangements of acetylenes and alkenes. Other approaches, such as radical reactions with halogenated alkenes, domino cyclizations, the smart use of epoxide-carbonyl rearrangements and intramolecular palladium-catalyzed ring contractions are discussed as well. A special section is dedicated to triptindanes, a subclass of [3.3.3]propellanes which are of interest to material sciences.

Verlagsausgabe §
DOI: 10.5445/IR/1000099177
Veröffentlicht am 06.03.2020
DOI: 10.1039/c8np00086g
Zitationen: 17
Web of Science
Zitationen: 18
Zitationen: 20
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2019
Sprache Englisch
Identifikator ISSN: 0265-0568, 1460-4752
KITopen-ID: 1000099177
Erschienen in Natural product reports
Verlag Royal Society of Chemistry (RSC)
Band 37
Seiten 224-245
Vorab online veröffentlicht am 29.05.2019
Nachgewiesen in Dimensions
Web of Science
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