Angewandte Chemie - International Edition p. 4767 - 4771 (2006)
Update date:2022-08-02
Topics:
Varseev, Georgy N.
Maier, Martin E.
(Chemical Equation Presented) An inside job: A Lewis acid induced intramolecular Diels-Alder (IMDA) reaction is used as the key step in the formation of symbioimine, an iminium alkaloid. The intermediate octahydronaphthalene is obtained from the IMDA reaction, after which extension of the aldehyde to a nitrile, alkylation of the nitrile, and imine formation allows for an efficient route to the target compound (see scheme; TBS = tert-butyldimethylsilyl).
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