Abstract
For quantitative and metabolic examination of sitosterol in plants, deuterio-labeled sitosterol and related steroids were synthesized from stigmasterol. The base-catalyzed enolization of a 3, 6-diketone group and reduction of the diketone with lithium aluminum deuteride were conducted as key reactions for the introduction of deuterium atoms into the steroidal A/B-ring. [2, 2, 3, 4, 4, 6, 7, 7-2H8] Sitosterol was obtained at 89% isotopic purity. The present labeling method for introducing eight deuterium atoms would appear, based on the present results, to be applicable to other sterols. Possible biosynthetic intermediate steroids from sitosterol to sitostanol were also prepared in deuterio-labeled form.
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