全合成
级联
化学
吗啡
纳米技术
立体化学
材料科学
药理学
生物
色谱法
作者
Shuyu Chu,Niels Münster,Tudor Balan,Martin D. Smith
标识
DOI:10.1002/anie.201608526
摘要
Morphine has been a target for synthetic chemists since Robinson proposed its correct structure in 1925, resulting in a large number of total syntheses of morphine alkaloids. Here we report a total synthesis of (±)-morphine that employs two key strategic cyclizations: 1) a diastereoselective light-mediated cyclization of an O-arylated butyrolactone to form a tricyclic cis-fused benzofuran and 2) a cascade ene-yne-ene ring closing metathesis to forge the tetracyclic morphine core. This approach enables a short and stereoselective synthesis of morphine in an overall yield of 6.6 %.
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