916225-97-3Relevant academic research and scientific papers
Total Synthesis of (±)-Thebainone A by Intramolecular Nitrone Cycloaddition
Hahn, Christian,Hennig, André,J?ger, Anne,Küttler, Thomas,Metz, Peter,Wang, Yuzhou
supporting information, (2020/04/21)
Using an intramolecular nitrone cycloaddition and a Heck cyclization as the crucial transformations, a total synthesis of the racemic morphine alkaloid thebainone A was accomplished in 22 steps commencing with isovanillin.
Total synthesis of (-)-morphine
Koizumi, Hifumi,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information; experimental part, p. 2192 - 2198 (2011/06/19)
We have developed an efficient total synthesis of (-)-morphine in 5% overall yield with the longest linear sequence consisting of 17 steps from 2-cyclohexen-1-one. The cyclohexenol unit was prepared by means of an enzymatic resolution and a Suzuki-Miyaura coupling as key steps. Construction of the morphinan core features an intramolecular aldol reaction and an intramolecular 1,6-addition. Furthermore, mild deprotection conditions to remove the 2,4-dinitrobenzenesulfonyl (DNs) group enabled the facile construction of the morphinan skeleton. We have also established an efficient synthetic route to a cyclohexenol unit containing an N-methyl-DNsamide moiety.
Total synthesis of (±)-morphine
Uchida, Kenji,Yokoshima, Satoshi,Kan, Toshiyuki,Fukuyama, Tohru
experimental part, p. 1219 - 1234 (2010/10/03)
The morphinan skeleton was effectively synthesized by an intramolecular Mannich-type reaction. Further transformation led to the total synthesis of morphine.
Total synthesis of (±)-morphine
Uchida, Kenji,Yokoshima, Satoshi,Kan, Toshiyuki,Fukuyama, Tohru
, p. 5311 - 5313 (2007/10/03)
The morphinan skeleton was effectively synthesized by an intramolecular Mannich-type reaction. Further transformation led to total synthesis of morphine.
