Juvenile hormone synthesis
- Reaction mechanism
- Supporting information
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An important demonstration of the use of fragmentation is the synthesis of juvenile hormone. Juvenile hormone contains three trisubstituted double bonds (one of which ends up as an epoxide), and the initial target was to make the related ketone which contains two of them. It was reasoned that if this methyl ketone could be made stereospecifically by fragmenting a cyclic starting material, the (hard-to-control) double bond stereochemistry would derive directly from the (easier-to-control) relative stereochemistry of the cyclic compound.