First diastereoselective total synthesis of bicyclic styryl lactone: (1R,5R,7R)-7-((E)-styryl)-2,6-dioxabicyclo[3.3.1]nonan-3-one

A concise and facile diastereoselective first total synthesis of bicyclic styryl lactone 1 is described in nine steps. This biologically active bicyclic styryl lactone was obtained in 8% overall yield from cinnamaldehyde 2 and (R)-3-hydroxyhex-5-enoic acid 3. Jacobsen resolution, Pinnick oxidation and Prins cyclisation reactions are the key steps involved in the synthesis.