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A Short and Efficient Synthesis of Bridgehead Mono‐ and Dideuteriated Tropinones
Author(s) -
Fournial Anaïs,
Ranaivondrambola Tsiresy,
MathéAllainmat Monique,
Robins Richard J.,
Lebreton Jacques
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901018
Subject(s) - hydroxylation , biosynthesis , chemistry , stereochemistry , deuterium , enzyme , mechanism (biology) , tropane , biochemistry , philosophy , physics , quantum mechanics , epistemology
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.