PubMed · 6306693
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E N Frankel. 1983. Volatile lipid oxidation products.. https://doi.org/10.1016/0163-7827(83)90002-4
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Shuffling of two simple building blocks and a regioselective transfer hydrogenation allow for the rapid synthesis of a small collection of lepidopteran sex pheromones, e.g., 8E,10Z-tetradeca-8,10-dienal 5c, from the horse chestnut leafminer (Cameraria ohridella).
The first enantiospecific total synthesis of the alkaloids 16-epi-vellosimine (1), (+)-polyneuridine (2), (+)-polyneuridine aldehyde (3), and macusine A (4) is reported. The key oxidation was accomplished with the Corey-Kim reagent to provide the important biogenetic intermediates, 16-epi-vellosimine (1) and polyneuridine aldehyde (3), the latter of which is required for the conversion of the sarpagan skeleton into the ajmalan system in the biosynthesis of quebrachidine. [reaction: see text].