38019-50-0Relevant articles and documents
Catalytic asymmetric allylation of ketones and a tandem asymmetric allylation/diastereoselective epoxidation of cyclic enones
Kim, Jeung Gon,Waltz, Karen M.,Garcia, Iliana F.,Kwiatkowski, David,Walsh, Patrick J.
, p. 12580 - 12585 (2004)
A simple procedure is reported for the catalytic asymmetric allylation of ketones, utilizing titanium tetraisopropoxide, BINOL, 2-propanol additive, and tetraallylstannane as allylating agent. A variety of ketone substrates, including acetophenone derivat
Hydroxy chalcogenide-promoted Morita-Baylis-Hillman Alkylation reaction: Intermolecular applications with alkyl halides as electrophiles
Gradillas, Ana,Belmonte, Efres,Da Silva, Rondes Ferreira,Perez-Castells, Javier
, p. 1935 - 1941 (2014/04/03)
Hydroxysulfides acted as catalysts to promote the Morita-Baylis-Hillman alkylation reaction of cyclohexenones and dihydropyridinones. The procedure worked efficiently with a variety of halides as electrophiles. Side reactions were in competition with the MBH alkylation, but fine-tuning the reaction conditions minimized their occurence.
An efficient method for construction of the angularly fused 6,3,5-tricyclic skeleton of mycorrhizin A and its analogues
Yu, Binxun,Jiang, Tuo,Quan, Weiguo,Li, Junpeng,Pan, Xinfu,She, Xuegong
supporting information; experimental part, p. 629 - 632 (2009/07/25)
(Chemical Equation Presented) The angularly fused 6,3,5-tricyclic system is readily generated via a cascade cyclization under acid promotion. The reaction proceeds at room temperature with high stereochemical fidelity from the electrophilic center of the
Divergent enantioselective synthesis of (-)-galanthamine and (-)-morphine
Trost, Barry M.,Tang, Weiping,Toste, F. Dean
, p. 14785 - 14803 (2007/10/03)
An efficient divergent synthetic strategy for the synthesis of the opiate and amaryllidaceae alkaloids emerges by employing a Pd-catalyzed asymmetric allylic alkylation (AAA) to set the stereochemistry. Three generations of syntheses of galanthamine are discussed in detail with particular focus on the scope of the palladium-catalyzed AAA reactions and intramolecular Heck reactions. The pivotal tricyclic intermediate is available in six steps from 2-bromovanillin and the monoester of methyl 6-hydroxycyclohexene-1-carboxylate. This intermediate requires only two steps to convert to (-)-galanthamine. Using a Heck vinylation, we found that the fourth ring of codeine/morphine could be formed. The final ring formation involves a novel visible light-promoted hydroamination. Thus, six steps are required to convert the pivotal tricyclic intermediate into codeine, which has been demethylated in high yield to morphine.
