Diastereoselective synthesis of allosecurinine and viroallosecurinine from menisdaurilide.
A new and versatile synthetic route to Securinega alkaloids is reported. The first synthesis of allosecurinine has been accomplished in seven steps and 40% yield, starting from (+)-menisdaurilide, using a vinylogous Mannich reaction as the key transformation. Similarly, viroallosecurinine has been synthesized from (-)-menisdaurilide.
Bardají
Gisela G
GG
Departament de Química, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
Cantó
Mariona
M
Alibés
Ramón
R
Bayón
Pau
P
Busqué
Félix
F
de March
Pedro
P
Figueredo
Marta
M
Font
Josep
J
D000470:Alkaloids / Q000138:chemical synthesis*; D001381:Azepines / Q000138:chemical synthesis*; D001572:Benzofurans / Q000737:chemistry*; D019665:Euphorbiaceae; D006572:Heterocyclic Compounds, Bridged-Ring / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D001381:Azepines; D001572:Benzofurans; D006572:Heterocyclic Compounds, Bridged-Ring; D007783:Lactones; D010880:Piperidines; C438745:menisdaurilide; C012607:virosecurinine; C000785:securinine