A short and efficient asymmetric synthesis of (±)-epi-cytoxazone from cis-(1R,2S,5R)-menthyl 4-methoxyphenylglycidates

Er, Mustafa2024-01-162024-01-162014-12Coşkun, N. F. ve Er, M. (2014). "A short and efficient asymmetric synthesis of (±)-epi-cytoxazone from cis-(1R,2S,5R)-menthyl 4-methoxyphenylglycidates". Chemistry of Natural Compounds, 50(6), 1071-1074.0009-31301573-8388https://doi.org/10.1007/s10600-014-1161-zhttps://link.springer.com/article/10.1007/s10600-014-1161-zhttps://hdl.handle.net/11452/39045The racemic epi-cytoxazone was synthesized, starting from p-anisaldehyde, in five steps and 48% overall yield. An efficient synthesis of azido alcohols has been achieved by regioselective ring opening of glycidates using NaN3 in MeOH-H2O. The key step of the process is reductive cyclization of azide carbonates by Zn-TMSCl.eninfo:eu-repo/semantics/closedAccess(±)-epi-cytoxazoneZn-TMSCl reduction4-methoxyphenylglycidateDarzen epoxidationAzidesStereoselective-synthesisCytokine modulator(+)-epi-cytoxazoneCytoxazone(-)-cytoxazonePharmacology & pharmacyChemistryA short and efficient asymmetric synthesis of (±)-epi-cytoxazone from cis-(1R,2S,5R)-menthyl 4-methoxyphenylglycidatesArticle0003457714000232-s2.0-8492210524210711074506Chemistry, medicinalChemistry, organicCytoxazone; Ester; Stereochemistry