Multi-step reaction with 10 steps
1: tetrahydrofuran / -60 - -10 °C
2: 39 percent / Novozyme 435 / 17 h / 40 °C
3: 92 percent / xylene / 0.25 h / 150 °C
4: Mn(OAc)3*2H2O; Cu(OAc)2; KOAc / acetic acid / 0.25 h / 70 °C
5: 54 percent / 2,6-di-tert-butylpyridine; Mg(ClO4)2 / 2.5 h / 120 °C
6: 88 percent / triflic anhydride; tetrabutylammonium bromide; sodium azide / sodium hydroxide / hexane; acetonitrile; H2O / 0.5 h / 0 °C
7: 83 percent / dirhodium tetraacetate / CH2Cl2 / 3 h / 20 °C
8: 13 percent / LiAlH4 / tetrahydrofuran / 0.33 h / 0 °C
9: 76 percent / 4-(N,N-dimethylamino)pyridine; triethylamine; mesyl chloride / CH2Cl2 / 49 h
10: 90 percent / potassium hydroxide / dioxane; methanol; H2O / 40 h / 50 °C
With
dmap; dirhodium tetraacetate; potassium hydroxide; lithium aluminium tetrahydride; sodium azide; 2,6-di-tert-butyl-pyridine; magnesium(II) perchlorate; copper diacetate; novozyme 435; trifluoromethylsulfonic anhydride; tetrabutylammomium bromide; potassium acetate; manganese triacetate; methanesulfonyl chloride; triethylamine;
sodium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; acetic acid; acetonitrile; xylene;
DOI:10.1021/jo035365r