Annulation of β-aryl-α-nitro-α,β-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

Abstract

A novel, highly stereocontrolled formal [3 + 3] annulation of β-aryl-α-nitro-α,β-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.