Diels-alder adducts of morphinan-6,8-dienes and their transformations “2279

HIGHLIGHTS

SUMMARY

    Morphine and its 3-O-methyl derivative codeine inhibit the cough reflex at several sites on the brainstem, with additional effects against construction of the upper airway, and opioids are widely used as cough suppressants and antitussive agents. Papaver somniferum is an abundant natural source of alkaloids with the morphinan skeleton, including neopine, thebaine, and oripavine, all of which are useful starting materials for pharmaceutically important derivatives (e_g, from 3: B/C-trans-morphinans, and from 4 and 5: naltrexone, nalbuphine, naloxone, etorphine, buprenorphine, and diprenorphine). The reaction of thebaine with maleic anhydride was . . .

     

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