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Article Dans Une Revue European Journal of Organic Chemistry Année : 2021

Total synthesis of phenanthropiperidine alkaloids by sequential alkylation of N,N-dibenzylaminoacetonitrile

Résumé

Two representative members of the phenanthropiperidine alkaloid family, tylophorine (1) and cryptopleurine (2), were synthesized by a bidirectional alkylation strategy employing dibenzylaminoacetonitrile as a substrate. This approach relies on the unprecedented condensation of metallated α-aminonitriles with bromomethylphenanthrenes to provide fully substituted α-aminonitriles, which are subjected to a NaBH4-mediated reductive decyanation process to form homobenzylic amines. From these intermediates, a terminal leaving group was introduced by simple chemical manipulation, and its displacement by a free primary amine under two favorable cyclization processes led to the formation of the future E-ring of both alkaloids in high yields. Finally, a late Pictet-Spengler cyclization ensured the formation of a D-ring for the alkaloids 1 and 2
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Dates et versions

hal-03480994 , version 1 (15-12-2021)

Identifiants

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Christelle Bouvry, Milène Franzetti, Jean-François Cupif, Jean-Pierre Hurvois. Total synthesis of phenanthropiperidine alkaloids by sequential alkylation of N,N-dibenzylaminoacetonitrile. European Journal of Organic Chemistry, 2021, 2021 (44), pp.6037-6051. ⟨10.1002/ejoc.202101131⟩. ⟨hal-03480994⟩
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