Enantioselective construction of 6-substituted-α,β-unsaturated-δ-lactone: total synthesis of anti-bacterial agent (−)-cleistenolide

An efficient and straightforward stereoselective synthesis of α,β-unsaturated lactone (1) cleistenolide is described. The synthesis was started from commercially available d-tartaric acid and completed within 13 steps with an overall yield of 7.92%. The cis-olefin was generated from Still–Gennari protocol and one of the hydroxyl groups was from dihydroxylation methodology. All the reactions were very clean and the products were obtained in very good yields.