Annulation of beta-aryl-alpha-nitro-alpha,beta-enals and 2,2-dimethyl-1,3-dioxan-5-one: a one-step assembly of nitrocyclitols. Application to a short practical synthesis of (+/-)-7-deoxy-2-epi-pancratistatin tetraacetate.
A novel, highly stereocontrolled formal [3 + 3] annulation of beta-aryl-alpha-nitro-alpha,beta-enals with the enamine derived from 2,2-dimethyl-1,3-dioxan-5-one and pyrrolidine afforded protected nitrocyclitols with five newly created stereocentres and constituted the key step in a short, gram-scale synthesis of a pancratistatin analogue.
Ortiz
Juan Carlos
JC
Departamento de Química Orgánica, Universidad de Santiago, 15782 Santiago de Compostela, Spain.
Ozores
Lidia
L
Cagide-Fagín
Fernando
F
Alonso
Ricardo
R