Proanthocyanidins, flavonoid oligomeric phytochemical antioxidants found in many plants such as blue berries, bilberries and grapes, yield--upon vigorous oxidation with KMnO4--equimolar quantities of 2,4,6-trihydroxybenzoic acid and 3,4-dihyrdoxybenzoic acid, which can then be effectively separated from the reaction mixture with an HPLC or, on a large scale, perhaps even by means of fractional distillation.
These two compounds yield TMA-6 and 3,4-DM(M)A after standard clandestine chemistry operations, keeping in mind that EtNO2 can be made from ethyl chloride.
Conclusion:
This procedure illustrates a novel synthetic pathway to these highly interesting compounds from natural products without having to perform a formylation as is currently the case from a reading of PIHKAL. Furthermore, the ubiquity of the starting materials in nature makes their future availability seem less uncertain, precluding of course all out nuclear annihilation at the hands of unthinking leaders on planet Earth in the near future.
