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Synthesis of New Morphinan Opioids by TBADT-Catalyzed Photochemical Functionalization at the Carbon Skeleton** |
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| Authors: | Dmitry Gorbachev Elliot Smith Dr. Stephen P. Argent Dr. Graham N. Newton Prof. Hon Wai Lam |
| Affiliation: | 1. The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU UK School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD UK Contribution: Conceptualization (equal), Data curation (lead), Formal analysis (lead), Methodology (lead), Writing - review & editing (equal);2. The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU UK School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD UK Contribution: Conceptualization (equal), Formal analysis (supporting), Investigation (supporting), Writing - review & editing (supporting);3. School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD UK;4. The GlaxoSmithKline Carbon Neutral Laboratories for Sustainable Chemistry, University of Nottingham, Jubilee Campus, Triumph Road, Nottingham, NG7 2TU UK |
| Abstract: | The synthesis of new morphinan opioids by the addition of photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring, is described. Using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the late-stage modification of complex, highly functionalized substrates. |
| Keywords: | late-stage functionalization morphinans opioids photocatalysis radical reactions |