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An Improved First‐Generation Synthesis of ent ‐Oxycodone
Author(s) -
EndomaArias Mary Ann A.,
Makarova Mariia,
Dela Paz Helen E.,
Hudlicky Tomas
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001320
Subject(s) - oxycodone , yield (engineering) , total synthesis , stereoselectivity , sequence (biology) , chemical synthesis , chemistry , stereochemistry , organic chemistry , materials science , catalysis , biochemistry , receptor , opioid , metallurgy , in vitro
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.