Catalytic Asymmetric Total Syntheses of (‒)-Morphine and (‒)-Codeine
YongQiang Tu and FuMin Zhang present the total syntheses of two analgesic drugs from commercially available but-3yn-1-ol.
(–)-Morphine is one of the most important and efficient analgesic drugs in the clinic and has been continuously ranked among the World Health Organization (WHO) model lists of essential medicines since 1977. Architecturally, (–)morphine possesses a synthetically challenging pentacyclic framework containing five contiguous stereocenters. Therefore, (–)morphine and several related alkaloids have attracted a considerable amount of research interest from the synthetic and pharmaceutical communities, and more than 30 total or formal synthetic routes have been reported. However, the catalytic and enantioselective total synthesis of (–)morphine has not been extensively explored yet and the asymmetric construction of the crucial allcarbon quaternary stereocenter remains a major challenge. Recently, the groups of Yong-Qiang Tu and FuMin Zhang from Lanzhou University (P. R. of China) reported the catalytic asymmetric total syntheses of (–)morphine and (–)codeine via a highly enantioselective Robinson annulation.
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