Reaction of rotenone with boron tribromide. Stereospecific2H-labelling of (–)-rotenonic acid in the 4′(E)-methyl group

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Abstract
Structural revisions are made to products formed when (–)-rotenone is treated with boron tri-bromide; stereospecific labelling of the 4′(E) methyl of (–)-rotenonic acid, a biosynthetic precursor of rotenone, can be achieved by treating product (4) with cyanoborodeuteride in hexamethylphosphorotriamide.