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Issue 40, 2006
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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

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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

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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, 4239-4241
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    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, 4239
    DOI: 10.1039/B606277F

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