Synthetic study on the angular triquinanes

The synthesis of an angular triquinane, which could serve as a suitable platform for the synthesis of several natural products (panaginsene, silphinene, senoxydene) is described. The synthesis is based on two consecutive cyclopentene annulations, where alkenes were used as latent carbonyl functional...

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Bibliographic Details
Published in:Journal of the Serbian Chemical Society 2023, Vol.88 (10), p.975-983
Main Authors: Stjepanovic, Mihailo, Jankovic, Aleksandar, Vulovic, Bojan, Matovic, Radomir, Saicic, Radomir
Format: Article
Language:English
Subjects:
aldol condensation
cyclopentane
natural products
organic synthesis
wacker oxidation
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Summary:The synthesis of an angular triquinane, which could serve as a suitable platform for the synthesis of several natural products (panaginsene, silphinene, senoxydene) is described. The synthesis is based on two consecutive cyclopentene annulations, where alkenes were used as latent carbonyl functionalities (via Wacker reaction), and cyclopentenone annulation was effected by aldol condensation.
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC230627046S