A convergent stereocontrolled synthesis of [3-(14) C]solanesol
Stephen J Roe1, Mark F Oldfield, Neil Geach
1Selcia Ltd, Fyfield Business & Research Park, Fyfield Road, Ongar, Essex, CM5 0GS, UK.
Abstract:
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 ). 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 ) 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)
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Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...


