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.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry