201025-90-3Relevant academic research and scientific papers
Selective one-pot carvone oxime hydrogenation over titania supported gold catalyst as a novel approach for dihydrocarvone synthesis
Demidova, Yu. S.,Suslov,Simakova,Volcho,Salakhutdinov,Simakova,Murzin, D. Yu.
, p. 142 - 148 (2016)
It was shown for the first time that dihydrocarvone can be selectively produced by gold-catalyzed one-pot transformation of carvone oxime. This reaction was carried out at 100 °C under hydrogen pressure of 9 bar over 1.9 wt.% Au/TiO2 catalyst using methanol as a solvent. Dihydrocarvone synthesis was shown to occur via carvone formation with the subsequent hydrogenation of its conjugated C=C double bond. Application of Au/TiO2 catalyst for both deoximation and selective hydrogenation of olefinic C=C functional group is reported for the first time. The combination of these steps provides optimization of the synthetic method for dihydrocarvone production from carvone oxime which is a key intermediate in carvone synthesis from limonene. Despite a lower reaction rate than in the case of carvone, a significant increase in the stereoselectivity towards trans-dihydrocarvone was observed in the case of carvone oxime hydrogenation. The ratio between trans- and cis-dihydrocarvone was close to 4.0 compared to 1.8 achieved in the case of carvone hydrogenation.
Syntheses and absolute configurations of the marine sponge purines (+)-agelasimine-A and (+)-agelasimine-B
Ohba, Masashi,Iizuka, Kazuaki,Ishibashi, Hiroyuki,Fujii, Tozo
, p. 16977 - 16986 (1997)
The first total syntheses of (+)-agelasimine-A and (+)-agelasimine-B, adenine-related bicyclic diterpenoids isolated from the marine sponge Agelas mauritiana, have been achieved via a highly stereoselective route. On the basis of the present results, the absolute configurations of both alkaloids have been defined as shown in stereoformulas (+)-1a and (+)-1b, respectively.
