Total synthesis of (±)-anatoxin-a via N-acyliminium intermediates
1986; Elsevier BV; Volume: 27; Issue: 39 Linguagem: Inglês
10.1016/s0040-4039(00)85068-6
ISSN1873-3581
AutoresKaren H Melching, Henk Hiemstra, Wim J. Klaver, W. N. SPECKAMP,
Tópico(s)Chemical synthesis and alkaloids
Resumo(±)Anatoxin-a has been synthesized in 8 steps, starting from succinimide, 4-bromo-1-butene and dimethyl (2-oxopropyl)phosphonate, by employing as the key step an intramolecular reaction of an N-acyliminium precursor with an α,β-unsaturated ketone moiety, induced by saturated HCl in MeOH at −50°C.
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