A Convergent Stereocontrolled Synthesis Of [3-C-14]Solanesol

In this communication, we report the synthesis of similar to 5mCi of [3-C-14]solanesol (1) prepared from ethyl [3-C-14]acetoacetate and (all-E)-octaprenyl bromide (2) in four steps, with a specific radioactivity of 19.83mCi/mmol and with a chemical/stereochemical and radiochemical purity of 95%. (Figure). Position 3 of the chain was selected for C-14 labelling because of the metabolic stability of this position. Unlabelled (all-E)-octaprenyl (18) (Scheme) necessary for this work was prepared via a convergent iterative allyl-allyl' coupling approach of precursors easily derived from readily available inexpensive starting materials.(1) Copyright (c) 2013 John Wiley & Sons, Ltd.