An Improved First‐Generation Synthesis of ent‐Oxycodone. Issue 27 (20th July 2020)

• Record Type: Journal Article
• Authors: Endoma‐Arias, Mary Ann A.; Makarova, Mariia; Dela Paz, Helen E.; Hudlicky, Tomas
• Is Part Of: ChemistrySelect. Volume 5:Issue 27(2020)
• Page Start: 8241
• Page End: 8245
• Publication Date: 2020-07-20
• Subjects: cyclic carbonate -- elimination -- Heck reaction -- microbial dihydroxylation -- Mitsunobu reaction -- oxycodone -- pinacol-type coupling; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202001320
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: An improvement in the stereoselective total synthesis of unnatural (+)‐oxycodone from phenethyl acetate is described. The total step count was reduced by conducting some chemical transformations in "one‐pot" and a change in the sequence of chemical operations was implemented, in comparison with the previously published first‐generation synthesis. The synthesis of (+)‐oxycodone was completed in a total of 12 operations (17 steps) and an overall yield of 1.6%, in comparison to our previous synthesis (13 operations, 19 steps, 1.5% yield) Experimental and spectral data are provided for all new compounds. Abstract : A slight modification in the preparation of unnatural (+)‐oxycodone from phenethyl acetate resulted in the improvement of the overall yield and in the total number of operations. By changing the sequence of chemical steps, the need for protection‐deprotection steps was eliminated and a more efficient synthesis was accomplished.