509-66-0Relevant articles and documents
Total Synthesis of (?)-Morphine
Umihara, Hirotatsu,Yokoshima, Satoshi,Inoue, Masayuki,Fukuyama, Tohru
, p. 6993 - 6995 (2017/05/29)
Asymmetric total synthesis of (?)-morphine has been accomplished in 18 steps from commercially available 7-methoxy-2-tetralone. Our synthesis features a simple transformation from a readily prepared chiral intermediate, construction of the E-ring by acid-mediated cyclization, and singlet oxygen-mediated manipulation of the C-ring. Transformation of the final stage involves construction of the morphinan skeleton by means of 1,6-addition of in situ generated secondary amine.
Total synthesis of (-)-morphine
Koizumi, Hifumi,Yokoshima, Satoshi,Fukuyama, Tohru
, 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.
Formation of the Neopinone/Codeinone Ring System via Intramolecular 1,6-Addition of an Amino Moiety to a Dienyl Ketone
Toth, J. E.,Fuchs, P. L.
, p. 2594 - 2596 (2007/10/02)
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