Biomimetic Approaches to Morphine Alkaloids. Total Synthesis of (+/-)-2-Hydroxycodeine and (+/-)-Noroxycodone

Article abstract of DOI:10.1021/jo00335a079

Oxidative coupling of a triphenolic hydroxynorreticuline substrate with VOCl3 affords the corresponding 2-hydroxynorsalutaridine derivative in good yield; the latter is readily converted to the title compounds via (+/-)-N-(ethoxycarbonyl)-2-hydroxynorthebaine.