Synthesis and evaluation of the antitumor properties of esters of 2-furoic acid and 2-furylacrylic acid
A series of activated and nonactivated esters of 2-furoic and 2-furylacrylic acids were synthesized and examined for antineoplastic activity in the Ehrlich ascites carcinoma screen at 20 mg/kg/d. 2-Furoic acid and 2-furylacrylic acid demonstrated potent activity, as did the methyl and cyanomethyl esters of each series. The vinyl ester of 2-furoic acid possessed antineoplastic activity. However, the ethyl and D,L-tetrahydropyranyl esters of each series were inactive in the tumor screen.
Regio- and Stereoselective Chan-Lam-Evans Enol Esterification of Carboxylic Acids with Alkenylboroxines
Efficient and scalable Cu(II)-mediated enol esterification methodology of carboxylic acids from alkenyl boroxines and boronic acids is presented. The reaction shows a wide scope in aliphatic and aromatic carboxylic acids in combination with several alkenyl boroxines. In the case of 2-substituted alkenyl boroxines the double bond configuration was fully retained in the enol ester product. Also N-hydroxyimides and imides could be transformed in the respective amidooxy vinyl enol ethers and vinyl enamides. Finally, with the exception of methionine, all other 19 canonical amino acids showed their compatibility to give the enol esters in a stereoselective fashion. (Figure presented.).
Steemers, Luuk,Wijsman, Linda,van Maarseveen, Jan H.
supporting information
p. 4241 - 4245
(2018/10/02)
Dinuclear zinc-catalyzed asymmetric desymmetrization of acyclic 2-substituted-1,3-propanediols: A powerful entry into chiral building blocks
The asymmetric acylation of meso-2-substituted-1,3-propanediols by using an amphoteric chiral dinuclear zinc catalyst is described. It is has been demonstrated that both 2-alkyl- and 2-aryl-1,3-propanediols can be desymmetrized in high yields and enantioselectivities by using the same family of ligands. Given that both antipodes of the chiral catalyst are available, both enantiomers of the desymmetrized product can be obtained from the same starting material. The synthetic utility of the desymmetrized products has been demonstrated by the synthesis of several chiral building blocks with high enantiomeric purities.
Trost, Barry M.,Malhotra, Sushant,Mino, Takashi,Rajapaksa, Naomi S.
scheme or table
p. 7648 - 7657
(2009/08/19)
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