735269-96-2Relevant articles and documents
A simple and efficient synthesis of (±)-mesembrine
Chavan, Subhash P.,Khobragade, Dushant A.,Pathak, Ashok B.,Kalkote
, p. 5263 - 5265 (2004)
A simple and efficient synthesis of (±)-mesembrine 1 is described employing double Michael addition and as the key step in 18% overall yield.
An efficient and scalable one-pot double Michael addition-Dieckmann condensation for the synthesis of 4,4-disubstituted cyclohexane β-keto esters
DeGraffenreid, Michael R.,Bennett, Sarah,Caille, Sebastien,De Turiso, Felix Gonzalez-Lopez,Hungate, Randall W.,Julian, Lisa D.,Kaizerman, Jacob A.,McMinn, Dustin L.,Rew, Yosup,Sun, Daqing,Yan, Xuelei,Powers, Jay P.
, p. 7455 - 7458 (2008/02/11)
(Chemical Equation Presented) A simple, scalable, and efficient one-pot methodology for the synthesis of 4,4-disubstituted cyclohexane β-keto esters from benzylic nitriles or esters and methyl acrylate promoted by potassium tert-butoxide is described. The process relies on a tandem double Michael addition-Dieckmann condensation reaction, which results in the formation of three discrete carbon-carbon bonds in a single pot, including a quaternary center. The method allows for the convenient and rapid synthesis of a variety of 4-aryl-4-cyano-2-carbomethoxycyclohexanone and 4-aryl-2,4- biscarbomethoxycyclohexanone building blocks for use in natural products synthesis and medicinal chemistry.