Abstract
Eight conformationally restricted LTD 4 analogues, 2a-d (n=1, 2), were prepared in nine steps from methyl 4-hydroxybenzoate (3). The key step in this approach is the Sharpless asymmetric epoxidation of allylic alcohol 8 in which all four possible epoxy alcohol diastereomers 9a-d were prepared. A single-crystal X-ray analysis of 9b and application of the Sharpless model for predicting epoxidation stereoselectivity led to the assignment of relative stereochemistry and absolute configuration of 9a-d. These high optical purity epoxy alcohols were then converted to chiral LTD 4 analogues 2a-d (n=1, 2) in three steps
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