The first total synthesis of (-)-lipstatin

Article abstract of DOI:10.1021/jo00127a045

A key step in the first total synthesis of the potent pancreatic lipase inhibitor (-)-lipstatin (1) is a diastereoselective Lewis acid-promoted [2 + 2] cycloaddition reaction between n-hexyl(trimethylsilyl)ketene (4) and (R)-(-)-(Z,Z)-3-[(tert-butyldimethylsilyl)oxy]-5,8-tetradecadienal (3), which is prepared from dimethyl (S)-(-)-malate.