Rapid access to tetracyclic ring system of lennoxamine type natural product by combined use of a novel three-component reaction and Pummerer cyclization.
From readily available allylamine, aldehyde and isocyanoacetamide, a three-component reaction followed by a Pummerer cyclization provided tetracyclic ring systems (6-7-5-6 and 6-6-5-6) in excellent overall yields.
Gámez Montaño
Rocio
R
Institut de Chimie des Substances Naturelles, 91198 Gif-sur-Yvette, France.
Zhu
Jieping
J
D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004146:Dioxanes / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis
D004146:Dioxanes; D006571:Heterocyclic Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; C442893:lennoxamine