Stereoselective synthesis of anti-1,3-diol units via Prins cyclisation:: application to the synthesis of (-)-sedamine

The scope of the Prins cyclisation, the higher stereoselective synthesis of multisubstituted tetrahydropyrans front aldehydes and homoallylic alcohols, is expanded. A new approach for the stereoselective synthesis of polyketide precursors containing anti-1,3-diols, flanked by a variety of alkyl branches and functional groups is described. The approach is successfully exploited for the synthesis of (-)-sedamine. (c) 2006 Elsevier Ltd. All rights reserved.