Asymmetric synthesis of the C3-C8 fragment of leucotrienes and analogues

Article abstract of DOI:10.1055/s-1991-26622

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-trimethyls ilyl-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.