569340-56-3Relevant academic research and scientific papers
Ruthenium-catalyzed addition of primary amides to alkynes: A stereoselective synthesis of secondary enamides
Goossen, Lukas J.,Blanchot, Mathieu,Salih, Kifah S. M.,Goossen, Kaethe
experimental part, p. 2283 - 2288 (2009/12/27)
The anti-Markovnikov addition of primary amides to terminal alkynes under the formation of Z-configured secondary enamides is efficiently promoted by a catalyst system generated in situ from bis(2-methallyl)(cycloocta-1,5-diene) ruthenium(II), 1,4-bis(dic
Synthesis of secondary enamides by ruthenium-catalyzed selective addition of amides to terminal alkynes
Goossen, Lukas J.,Salih, Kifah S. M.,Blanchot, Mathieu
supporting information; experimental part, p. 8492 - 8495 (2009/05/11)
(Chemical Equation Presented) Enamides made easy: A catalyst system generated in situ using bis(2-methallyl)-(cycloocta-1,5-diene)ruthenium(II), 1,4-bis(dicyclohexylphosphino)butane, and ytterbium triflate efficiently catalyzes the addition of primary amides to terminal alkynes, selectively forming the Z-anti-Markovnikov enamides. The E isomers are also accessible by combining the hydroamidation with an in situ double-bond isomerization reaction.
Lobatamide C: Total synthesis, stereochemical assignment, preparation of simplified analogues, and V-ATPase inhibition studies
Shen, Ruichao,Lin, Cheng Ting,Bowman, Emma Jean,Bowman, Barry J.,Porco Jr., John A.
, p. 7889 - 7901 (2007/10/03)
The total synthesis and stereochemical assignment of the potent antitumor macrolide lobatamide C, as well as synthesis of simplified lobatamide analogues, is reported. Cu(I)-mediated enamide formation methodology has been developed to prepare the highly unsaturated enamide side chain of the natural product and analogues. A key fragment coupling employs base-mediated esterification of a β-hydroxy acid and a salicylate cyanomethyl ester. Three additional stereoisomers of lobatamide C have been prepared using related synthetic routes. The stereochemistry at C8, C11, and C15 of lobatamide C was assigned by comparison of stereoisomers and X-ray analysis of a crystalline derivative. Synthetic lobatamide C, stereoisomers, and simplified analogues have been evaluated for inhibition of bovine chromaffin granule membrane V-ATPase. The salicylate phenol, enamide NH, and ortho-substitution of the salicylate ester have been shown to be important for V-ATPase inhibitory activity.
