Abstract
AbstractThe methyl ester rac‐4a of (5R*,6S*)‐5,6‐dihydroxyhexadecanoic acid was prepared by a Wittig reaction of (4‐carboxybutyl)triphenylphosphonium bromide (2) with undecanal (1) followed by esterification with methanol and cis dihydroxylation with osmium (VIII) oxide/N‐methylmorpholine N‐oxide. After conversion of the dihydroxy ester rac‐4a into (5R*,6S*)‐6‐hydroxyhexadecan‐5‐olide (rac‐5) by lactonization (5R,6S)‐6‐acetoxyhexadecan‐5‐olide (6), the mosquito oviposition attractant pheromone, was obtained by an enantioselective lipase‐catalyzed acetylation with vinyl acetate. In an alternative route the dihydroxy ester rac‐4a was subjected to a lipase‐catalyzed lactonization, which afforded as the main product (5S,6R)‐6‐hydroxyhexadecan‐5‐olide (ent‐5), the enantiomer of the deacetylated pheromone.
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