An efficient, practical, and stereocontrolled synthesis of (Z)‐civetone (1), a representative musk perfume, has been performed utilizing a Ti‐Dieckmann (intramolecular Ti‐Claisen) condensation of dimethyl (Z)‐9‐octadecenedioate (3) as the key step. This cyclization reaction has some advantages compared with the traditional basic Dieckmann condensation such as higher concentration (100–300 mM), lower reaction temperature (0–5 °C), shorter reaction time (1–3 h), use of environmentally benign (low toxicity and safe) reagents (TiCl4 and Et3N or Bu3N), and economical reagents and solvents. 15‐, 17‐, and 19‐membered saturated β‐ketoesters (6–8) were also prepared by the present method.
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SUMMARYCoccidian oocysts were detected in the vaginal excreta of a Holstein cow, about 2 years old, kept in Kawasaki City, Kanagawa Prefecture, Japan. The oocysts were identified as those of Eimeria zuernii by their morphological characteristics and sporulation time. The oocysts isolated from the excreta were orally administered, with cattle milk substitutes, to a new-born Holstein male calf in doses of 104 and 560 on day 21 and day 106 after birth respectively. Fecal examinations were performed for oocysts every day from the administration of oocysts to the necropsy on day 108 after administration or day 128 after birth. Pathological examinations revealed no changes in any of the organs possibly affected by coccidian infection, and no protozoan parasites were detected by histopathological examination in the tissues of the digestive tract, eyes and periorbital tissues, and reproductive organs.
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