A convergent stereocontrolled synthesis of [3‐ 14 C]solanesol

In this communication, we report the synthesis of ~5 mCi of [3‐ 14 C]solanesol (1) prepared from ethyl [3‐ 14 C]acetoacetate and (all‐ E )‐octaprenyl bromide (2) in four steps, with a specific radioactivity of 19.83 mCi/mmol and with a chemical/stereochemical and radiochemical purity of ≥ 95%. (Figure [Figure 1. Retrosynthetic analysis of [3‐14C]Solanesol (1). ...]). Position 3 of the chain was selected for 14 C labelling because of the metabolic stability of this position. Unlabelled (all‐ E )‐octaprenyl (18) (Scheme [Scheme 4. Scheme Synthesis of precursor (2). Conditions: a) cat. 3‐chlorosalicylic ...]) 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 © 2013 John Wiley & Sons, Ltd.