Synthesis of 4, 6-dialkyl-1,3-dioxins. Versatile intermidiates for the preparation of (E)-alkenones, anti,anti-1, 2, 3-triols and syn-1, 3-diols

Raymond L. Funk, Gary L. Bolton

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Abstract

The title compounds 4 are prepared from 4-alkyldioxins 2 via a metalation, alkylation sequence. The dialkyl dioxins 4 are thermally labile (providing enones) and undergo highly stereoselective hydroboration or hydrogenation reactions to provide anti, anti-1, 2, 3-triols and syn, 1, 3-diols, respectively. This methodology has been exploited in the synthesis of (±)-endo-1, 3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.

Original languageEnglish (US)
Pages (from-to)1111-1114
Number of pages4
JournalTetrahedron Letters
Volume29
Issue number10
DOIs
StatePublished - 1988

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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