916225-92-8Relevant academic research and scientific papers
Total synthesis of (±)-morphine
Uchida, Kenji,Yokoshima, Satoshi,Kan, Toshiyuki,Fukuyama, Tohru
, p. 1219 - 1234 (2009)
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
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.
Synthesis of santiagonamine
Markey, Michael D.,Ying, Fu,Kelly, T. Ross
, p. 3255 - 3257 (2008/02/11)
The first total synthesis of santiagonamine (1) is achieved in 12 steps from isovanillin. A palladium-catalyzed Ullmann cross-coupling reaction and a photocyclization are the key steps in the synthesis.
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.
