Journal of Organic Chemistry p. 12209 - 12215 (2019)
Update date:2022-08-31
Topics:
Nagasawa, Shota
Jones, Kerry E.
Sarpong, Richmond
Herein, we describe an enantiospecific route to one enantiomer of a common decalin core that is present in numerous highly oxygenated terpenoids. This intermediate is accessed in eight steps from (R)-carvone, an inexpensive, enantioenriched building block, which can be elaborated to the desired bicycle through sequential Fe(III)-catalyzed reductive olefin coupling and Dieckmann condensation. The same synthetic route may be applied to (S)-carvone to afford the enantiomer of this common intermediate for other applications.
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