title: A convergent stereocontrolled synthesis of [3-(14) C]solanesol.
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)
authors.affiliation: Selcia Ltd, Fyfield Business & Research Park, Fyfield Road, Ongar, Essex, CM5 0GS, UK.
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Roe
authors.forename: Mark F
authors.initials: MF
authors.lastname: Oldfield
authors.forename: Neil
authors.initials: N
authors.lastname: Geach
authors.forename: Andrew
authors.initials: A
authors.lastname: Baxter
mesh_terms: D002250:Carbon Radioisotopes / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D002250:Carbon Radioisotopes; D013729:Terpenes; C017719:solanesol
keywords: carbon-14; convergent synthesis; solanesol; stereocontrolled