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Synthesis 1991; 1991(11): 979-982
DOI: 10.1055/s-1991-26622
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Asymmetric Synthesis of the C3-C8 Fragment of Leucotrienes and Analogues

Guy Solladie* , Chafiq Hamdouchi
  • *Ecole Européenne des Hautes Eudes des Industries Chimiques (URA du CNRS 466), F-67008 Strasbourg, France
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Publikationsdatum:
29. April 2002 (online)

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An asymmetric synthesis of the C3-C8 fragment of leukotrienes and analogues using the aldol-type condensation of chiral sulfinyl ester is described. Thus, starting from (3S)-3-tert-butyldimethylsiloxy-1-(2-methoxyethoxymethoxy)-5-trimethylsilyl-4-pentyne, the corresponding methyl (2Z,4S)-hexenoate, methyl (4R)-hexanoate, (2Z,4S)- and (2E,4S)-2-hexenal derivatives were prepared. Several molecules prepared during this work were shown to be important intermediates in the synthesis of various natural products.