期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 46, 页码 14304-14307出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201608526
关键词
cascade reactions; metathesis; morphine; photochemistry; total synthesis
资金
- ERC [259056]
- Deutsche Forschungsgemeinschaft [MU 3987/1-1]
- EPSRC Centre for Doctoral Training in Synthesis for Biology and Medicine [EP/L015838/1]
- Engineering and Physical Sciences Research Council [1651574] Funding Source: researchfish
- European Research Council (ERC) [259056] Funding Source: European Research Council (ERC)
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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