The β-lactone moiety of (–)-lipstatin 1, a potent inhibitor of pancreatic lipase, is prepared via a Lewis acid-promoted [2 + 2] cycloaddition between hexyltrimethylsilyl ketene 3 and the (Z,Z)-dienic aldehyde 4, obtained from hexanal by two stereoselective Wittig reactions.
J. Pons, A. Pommier, J. Lerpiniere and P. Kocienski, J. Chem. Soc., Perkin Trans. 1, 1993, 1549 DOI: 10.1039/P19930001549
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