A short and efficient asymmetric synthesis of (±)-epi-cytoxazone from cis-(1R,2S,5R)-menthyl 4-methoxyphenylglycidates
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Date
2014-12
Authors
Er, Mustafa
Journal Title
Journal ISSN
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Publisher
Springer
Abstract
The 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.
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Keywords
(±)-epi-cytoxazone, Zn-TMSCl reduction, 4-methoxyphenylglycidate, Darzen epoxidation, Azides, Stereoselective-synthesis, Cytokine modulator, (+)-epi-cytoxazone, Cytoxazone, (-)-cytoxazone, Pharmacology & pharmacy, Chemistry
Citation
Coşkun, 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.