Enantioselective approach to securinega alkaloids. Total synthesis of securinine and (-)-norsecurinine

David González-Gálvez, Elena García-García, Ramon Alibés, Pau Bayón, Pedro De March, Marta Figueredo, Josep Font

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45 Citations (Scopus)

Abstract

(Chemical Equation Presented) The most representative securinega alkaloids have been synthesized through a new strategy involving the palladium-catalyzed enantioselective allylation of a cyclic imide, a vinylogous Mannich reaction, and a ring-closing metathesis process, as the key steps. The diastereoselectivity of the vinylogous Mannich reaction was in partial agreement with DFT theoretical calculations performed in a model system. The synthesis of (-)-norsecurine has been accomplished in nine steps from succinimide and 14% overall yield and that of securinine in 10 steps from glutarimide and 20% overall yield. Both syntheses compare favorably with those previously described. The three key transformations have been performed in a synthetically useful scale (more than 500 mg). Moreover, since the enantioselectivity was originated by a chiral phosphine ligand, the antipode of which is readily available, the same route is expected to give access to (+)-norsecurinine and virosecurinine. © 2009 American Chemical Society.
Original languageEnglish
Pages (from-to)6199-6211
JournalJournal of Organic Chemistry
Volume74
Issue number16
DOIs
Publication statusPublished - 21 Sep 2009

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