Multi-step reaction with 18 steps
1.1: dioxane / Photolysis
2.1: BF3*OEt2 / benzene / 25 °C
3.1: DBU; CS2; CH3I / dimethylformamide / 0 - 20 °C
3.2: 86 percent / Bu3SnH; AIBN / toluene / 120 °C
4.1: LDA; PhSeBr / tetrahydrofuran / 4 h / -78 °C
4.2: 86 percent / aq. H2O2 / methanol / 2 h / 20 °C
5.1: OsO4; K3Fe(CN)6 / H2O; 2-methyl-propan-2-ol / 20 h / 20 °C
6.1: 96 percent / PTSA / CH2Cl2 / 0 - 20 °C
7.1: 84 percent / aq. NaOH / methanol / 1 h / 0 °C
8.1: 95 percent / NaH / dimethylformamide / 0 - 20 °C
9.1: 36 h / -78 - 0 °C
10.1: Dess-Martin agent; aq. NaHCO3 / CH2Cl2 / 2 h / 20 °C
11.1: 82 percent / TiCl; Zn / CH2Cl2 / 25 °C
12.1: NH2OH / ethyl acetate / 20 °C
13.1: 98 percent / CAN / acetonitrile; H2O / 0.5 h / 0 °C
14.1: DIAD; HCO2H; Ph3P
14.2: 92 percent / NaBH4 / methanol
15.1: 87 percent / t-BuOOH; Ti(iPrO)4 / H2O; 2-methyl-propan-2-ol / 20 h / 20 °C
16.1: SOCl2; pyridine / tetrahydrofuran / 0 - 20 °C
16.2: 57 percent / SeO2 / acetonitrile / 36 h / 20 °C
17.1: 83 percent / IBX / dimethylsulfoxide / 20 h / 85 °C
18.1: 95 percent / AcCl / methanol / 6 h / 0 °C
With
pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; carbon disulfide; sodium hydroxide; osmium(VIII) oxide; formic acid; thionyl chloride; ammonium cerium(IV) nitrate; thallium chloride; di-isopropyl azodicarboxylate; Phenylselenyl bromide; boron trifluoride diethyl etherate; hydroxylamine; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; triphenylphosphine; potassium hexacyanoferrate(III); zinc; lithium diisopropyl amide; methyl iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
3.1: Barton deoxygenation / 14.1: Mitsunobu reaction / 15.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.03.072