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A convergent stereocontrolled synthesis of [3‐ 14 C]solanesol
Author(s) -
Roe Stephen J.,
Oldfield Mark F.,
Geach Neil,
Baxter Andrew
Publication year - 2013
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.3083
Subject(s) - chemistry , convergent synthesis , bromide , chemical synthesis , labelling , stereochemistry , radiochemistry , organic chemistry , biochemistry , in vitro
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.