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Updated: Aug 13, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
The stereochemistry of betulaprenol biosynthesis
Abstract:
By using stereospecifically double-labelled radioactive mevalonates it was shown that betulaprenols-6 to -9, found in the woody tissue of Betula verrucosa, each contain three biogenetically trans-isoprene residues and that the remaining residues are biogenetically cis. The results obtained with these radioactive mevalonates also indicated that the activity of isopentenyl pyrophosphate isomerase is low relative to the activity of prenyltransferase in this woody tissue. The incorporation of radioactive farnesyl pyrophosphate and radioactive geranylnerol and the lack of incorporation of radioactive geranylgeraniol into betulaprenols-6 to -9 demonstrated that they are formed by the cis-additions of isoprene residues to all-trans-farnesyl pyrophosphate.
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