A Short and Efficient Synthesis of Bridgehead Mono- and Dideuteriated Tropinones

摘要

Studies of the biosynthesis and degradation of alkaloids of the tropane class require substrates isotopically-labelled at specific positions. To investigate the mechanism of the enzyme reactions involved in the hydroxylation of the bridgehead position(s), compounds deuteriated at this position are needed. An efficient synthesis of 1,5-dideuterio- and racemic 1-deuteriotropinone is described in which high levels of deuterium are incorporated from the corresponding di- and mono-labelled 2,5-dibutoxytetrahydrofuran.