Some ring-opening reactions of a diepoxide derived from (−)-quinic acid

Synthesis of Polyamines from Ethylenediamine and Their Platinum(II) Complexes, Potential Antitumor Agents

“…The diepoxide 8 (not isolated) was prepared by treatment of ditosylate 7 with sodium methoxide in methanol according to the procedure previously described in the literature. [29] The ligand a and complex 9 were prepared as described in ref. [26] The ligands b-g were prepared in satisfactory yields by treating ethylenediamine with the corresponding intermediate (halide or epoxide) in ethanol at room temperature for 24 h. In the preparation of the ligand N,NЈ-bis(2-aminoethyl)-2-xylylenediamine (e), we have also isolated the ligand N-(2-aminoethyl)-isoindoline (f).…”

“…[29] Methanolic sodium methoxide (25 mmol of sodium in 10 mL of methanol) was slowly added to a solution of ditosylate 7 (5 g, 10.35 mmol) in methanol (15 mL). The reaction was stirred for 30 min at room temperature, concentrated under reduced pressure and added to chloroform (10 mL).…”

Quinic Acid as Versatile Chiral Scaffold in Organic Synthesis

“…4). The synthesis commenced with the multistep conversion of quinic acid to the TBS ether 52 (Scheme 7) [28]. Glycol cleavage of the diol system of 52 followed by elimination provided , unsaturated ketone 54 in excellent yield.…”

Studies on the Enzymatic Acylation of Quinic Acid, Shikimic Acid, Shikimic Acid, and Their Derivatives in Organic Solvents

“…The relatively small differences obtained in these calculations suggest that there are conformational equilibria in which C and D are present in comparable amounts. Although the determination of the preferred conformation in solution is only a prerequisite for the evaluation of substrate recognition by enzymes [14], the conformational interconversion of methyl shikimate (lOa) could be responsible for the loss of selectivity displayed by Ch.v. lipase, whose active site could have been approached by different conformers of this compound with similar stability.…”

“…Two other derivatives of quinic acid, the pentol 9a [14] and the quinide 4a [9], were also studied. In polyol 9a, Ch.u.…”