Synthesis of New Morphinan Opioids by TBADT‐Catalyzed Photochemical Functionalization at the Carbon Skeleton

Gorbachev, Dmitry; Smith, Elliot; Argent, Stephen P.; Newton, Graham N.; Lam, Hon Wai

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.

Citation

Gorbachev, D., Smith, E., Argent, S. P., Newton, G. N., & Lam, H. W. (2022). Synthesis of New Morphinan Opioids by TBADT‐Catalyzed Photochemical Functionalization at the Carbon Skeleton. Chemistry - A European Journal, 28(50), Article e202201478. https://doi.org/10.1002/chem.202201478

• Journal Article Type: Article
• Acceptance Date: Jun 3, 2022
• Online Publication Date: Jun 5, 2022
• Publication Date: Sep 6, 2022
• Deposit Date: Jun 6, 2022
• Publicly Available Date: Jun 6, 2023
• Journal: Chemistry - A European Journal
• Print ISSN: 0947-6539
• Electronic ISSN: 1521-3765
• Publisher: Wiley
• Peer Reviewed: Peer Reviewed
• Volume: 28
• Issue: 50
• Article Number: e202201478
• DOI: https://doi.org/10.1002/chem.202201478
• Keywords: General Chemistry; Catalysis; Organic Chemistry
• Public URL: https://nottingham-repository.worktribe.com/output/8391941
• Publisher URL: https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.202201478