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ChemicalBook CAS DataBase List CEPHALOTAXINE
24316-19-6

CEPHALOTAXINE synthesis

13synthesis methods
-

Yield:-

Steps:

Multi-step reaction with 15 steps
1.1: 87 percent / hydroxylamine hydrochloride; NaOH / ethanol; H2O / 3 h / Heating
2.1: 88 percent / LiAlH4; diisopropylamine / tetrahydrofuran / 4 h / Heating
3.1: 85 percent / triethylamine / tetrahydrofuran / 3 h / 25 °C
4.1: 76 percent / Cs2CO3 / dioxane / 18 h / Heating
5.1: 75 percent / Cs2CO3 / acetonitrile / 20 h / 25 °C
6.1: AgOTf / CH2Cl2 / 1 h / 25 °C
6.2: 77 percent / TBAT / CH2Cl2 / 20 h / -45 - 25 °C
7.1: 74 percent / samarium diiodide; HMPA / 2-methyl-propan-2-ol / 3 h / -78 - -45 °C
8.1: 99 percent / Schwartz's reagent / tetrahydrofuran / 16 h / Heating
9.1: 86 percent / KHMDS / tetrahydrofuran / 1 h / 0 °C
10.1: 99 percent / HCl; methanol / 16 h / 25 °C
11.1: Yb(OTf)3*xH2O / CH2Cl2 / 48 h / 0 °C
11.2: 50 percent / ortho-iodoxybenzoic acid / dimethylsulfoxide / 20 h / 25 °C
12.1: 42 percent / chromium(II) chloride / acetone; H2O / 1 h / 25 °C
13.1: 99 percent / hydrogen / Pd/C / ethyl acetate / 6 h / 25 °C
14.1: 55 percent / pTsOH*H2O / CH2Cl2 / 7 h / 0 - 25 °C
15.1: 95 percent / NaBH4; MeOH / 1.17 h / -78 - 25 °C

References:

Eckelbarger, Joseph D.;Wilmot, Jeremy T.;Gin, David Y. [Journal of the American Chemical Society,2006,vol. 128,# 32,p. 10370 - 10371]

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