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Synlett 1991; 1991(11): 781-782
DOI: 10.1055/s-1991-20872
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Asymmetric Synthesis of (-)-Tetrahydrolipstatin

Stephen C. Case-Green* , Stephen G. Davies, Charles J. R. Hedgecock
  • *The Dyson Perrins Laboratory, South Parks Road, Oxford OX1 3QY, England
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Publication Date:
07 March 2002 (online)

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The asymmetric synthesis of the β-propiolactone functionality of tetrahydrolipstatin was achieved via a stereoselective aldol reaction between the iron octanoyl complex (S)-[(η5-C5H5)Fe(CO)(PPh3)COC7H15] and (S)-3-benzyloxytetradecanal (obtained via a Noyori asymmetric hydrogenation of methyl 3-oxotetradecanoate) followed by oxidative decomplexation. Subsequent debenzylation and introduction of the N-formylleucine residue gave (-)-tetrahydrolipstatin.

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