Enantiospecific syntheses of leukotrienes C4, D4, and E4, and [14, 15-3H2] leukotriene E4 dimethyl ester

N Cohen, BL Banner, RJ Lopresti, F Wong…

Index: Cohen; Banner; Lopresti; et al. Journal of the American Chemical Society, 1983 , vol. 105, # 11 p. 3661 - 3672

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Citation Number: 83

Abstract

Abstract: A" chiral-pool" approach was employed to synthesize various leukotrienes (slow- reacting substance of anaphylaxis, SRS-A) enantiospecifically. The pivotal (S, S)-trans- epoxy alcohol 9 was prepared by efficient and facile routes starting from erythorbic acid (D- araboascorbic acid, 13). This epoxide could also be produced starting from D-glucose. The epimeric (S, R)-cis-epoxide 38 was obtained utilizing L-tartaric acid as the chiral starting ...