Abstract
The synthesis of 2,3-dihydroxy-3-{3-[3-(trifluoromethyl)diazirin-3-yl]phenyl}propionic acid (8), a new cleavable carbenegenerating reagent used in photocrosslinking experiments in molecular biology is described. This synthesis starts with the bromination of trifluoroacetophenone. The resulting compound 2 is converted into the corresponding diazirine 6 via oxime 3, O-tosyloxime 4, and diaziridinyl 5 derivatives. The cleavable cis-diol bond is formed via a cinnamic acid derivative 7 by permanganate oxidation resulting in the title compound 8.
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