Multi-step reaction with 11 steps
1.1: 92 percent / EtAlCl2 / toluene; hexane / 28 h / 20 °C
2.1: 89 percent / p-TsOH / benzene / 12 h / Heating
3.1: N-methylmorpholine-N-oxide; OsO4 / acetone; H2O / 216 h / 20 °C
3.2: 74 percent / NaIO4 / acetone; H2O / 1 h / 20 °C
4.1: 93 percent / m-chloroperbenzoic acid / CH2Cl2 / 72 h / 20 °C
5.1: 92 percent / p-TsOH / CH2Cl2 / 24 h / 20 °C
6.1: K2CO3 / methanol / 4 h / 20 °C
6.2: 90 percent / PCC / CH2Cl2 / 3 h / 20 °C
7.1: 88 percent / Et3N / CH2Cl2 / 0.5 h / -78 °C
8.1: 73 percent / Na2(EDTA); oxone; NaHCO3 / H2O; acetone; acetonitrile / 4 h / 20 °C
9.1: 79 percent / Al(OiPr)3 / toluene / 1 h / 20 °C
10.1: Me3SiCl; Et3N; DMAP / CH2Cl2 / 0.33 h / 20 °C
10.2: tetrahydrofuran / 0.17 h / -78 °C
10.3: 90 percent / HCl / tetrahydrofuran; H2O / 0.5 h / 20 °C
11.1: NaH / tetrahydrofuran / 0 - 20 °C
11.2: 86 percent / tetrahydrofuran / 12 h / Heating
With
dmap; Oxone; osmium(VIII) oxide; chloro-trimethyl-silane; ethylaluminum dichloride; edetate disodium; aluminum isopropoxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; toluene; acetonitrile; benzene;
1.1: Diels-Alder reaction / 4.1: Baeyer-Villiger oxidation;
DOI:10.1016/j.tet.2004.07.094