An asymmetric synthesis of (-)-tetrahydrolipstatin

Article abstract of DOI:10.1055/s-1994-25684

A key step in a short asymmetric synthesis of the potent pancreatic lipase inhibitor (-)-tetrahydrolipstatin (2) is a Lewis acid-catalysed [2 + 2] cycloaddition of n-hexyl(trimethylsilyl)ketene (5) to (R)-3-(tertbutyldimethylsilyloxy)tetradecanal (4a).