Multi-step reaction with 12 steps
1.1: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / 72 h / 20 °C
2.1: 92 percent / p-TsOH / CH2Cl2 / 24 h / 20 °C
3.1: K2CO3 / methanol / 4 h / 20 °C
3.2: 90 percent / PCC / CH2Cl2 / 3 h / 20 °C
4.1: 88 percent / Et3N / CH2Cl2 / 0.5 h / -78 °C
5.1: 73 percent / Na2(EDTA); oxone; NaHCO3 / H2O; acetone; acetonitrile / 4 h / 20 °C
6.1: 79 percent / Al(OiPr)3 / toluene / 1 h / 20 °C
7.1: Me3SiCl; Et3N; DMAP / CH2Cl2 / 0.33 h / 20 °C
7.2: tetrahydrofuran / 0.17 h / -78 °C
7.3: 90 percent / HCl / tetrahydrofuran; H2O / 0.5 h / 20 °C
8.1: NaH / tetrahydrofuran / 0 - 20 °C
8.2: 86 percent / tetrahydrofuran / 12 h / Heating
9.1: OsO4; N-methylmorpholine-N-oxide / acetone; H2O / 96 h / 20 °C
9.2: 78 percent / NaIO4 / acetone; H2O / 48 h / 20 °C
10.1: 70 percent / H2 / Pd/C / ethyl acetate
11.1: 100 percent / NaBH4 / methanol / 0.5 h / 0 °C
12.1: 2,4,6-collidine; MsCl / CH2Cl2 / 48 h / 0 °C
12.2: 83 percent / NaH / tetrahydrofuran / 4 h / Heating
With
2,4,6-trimethyl-pyridine; dmap; Oxone; sodium tetrahydroborate; osmium(VIII) oxide; chloro-trimethyl-silane; hydrogen; edetate disodium; aluminum isopropoxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
1.1: Baeyer-Villiger oxidation;
DOI:10.1016/j.tet.2004.07.094