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

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Akademik Birimler

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Coşkun, Necdet F.

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Er, Mustafa

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Springer

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Özet

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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(±)-epi-cytoxazone, Zn-TMSCl reduction, 4-methoxyphenylglycidate, Darzen epoxidation, Azides, Stereoselective-synthesis, Cytokine modulator, (+)-epi-cytoxazone, Cytoxazone, (-)-cytoxazone, Pharmacology & pharmacy, Chemistry

Alıntı

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.

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