2859-02-1Relevant articles and documents
A desymmetrization-based approach to morphinans: application in the total synthesis of oxycodone
Park, Kun Ho,Chen, David Y.-K.
, p. 13018 - 13021 (2018)
Here we report a total synthesis of the pharmacologically significant morphinan alkaloid, oxycodone. The centerpiece of the developed strategy features the first application of the Rovis desymmetrization of peroxyquinol in target-oriented total synthesis to access an optically active phenanthrene framework shared by the morphinans. A Stork-Ueno radical cyclization under photoredox conditions installed the all-carbon quaternary stereocenter, and a late-stage reductive detosylation with concomitant piperidine formation secured the core structure of the target molecule.
METHOD OF PREPARING BUPRENORPHINE
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Paragraph 0157; 0158, (2014/09/03)
An improved process for preparing buprenorphine and a method for increasing the yield of buprenorphine or a derivative thereof.
L-Selectride as a general reagent for the O-demethylation and N- decarbomethoxylation of opium alkaloids and derivatives
Coop,Janetka,Lewis,Rice
, p. 4392 - 4396 (2007/10/03)
L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N- decarbomethoxylation and O-demethylation in one pot, or only render N- decarbomethoxylation in high yield without accompanying O-demethylation.