Abstract
Reaction of the Diazoketone 1 derived from the tricyclic diterpene Pleuromutilin with elemental Fluorine in CFCl 3/CHCl 3 at −60° C led to the formation of several fluorinated-products ( 2 – 4 ). Using pure CFCl 3 as solvent did not result in any isolable product, while the addition of solid KF to the reaction solution increased the yield markedly. Reacting 1 with liquid HF in CH 2Cl 2 at −70° C gave mainly the 2-Fluoropleuromutilin 3 together with the corresponding α,β-unsaturated ketone 5 which reacts further to yield the rearrangement product 6 . ▪
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