Jump to main content
Jump to site search

Issue 40, 2006
Previous Article Next Article

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

Author affiliations

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.

Graphical abstract: 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

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Jun 2006, accepted on 31 Jul 2006 and first published on 31 Aug 2006


Article type: Communication
DOI: 10.1039/B606277F
Citation: Chem. Commun., 2006,0, 4239-4241
  •   Request permissions

    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

    J. C. Ortiz, L. Ozores, F. Cagide-Fagín and R. Alonso, Chem. Commun., 2006, 0, 4239
    DOI: 10.1039/B606277F

Search articles by author

Spotlight

Advertisements