Multi-step reaction with 18 steps
1.1: Bu2SnO / toluene; methanol / 14 h / 55 °C
1.2: Et3N / dioxane / 4 h / 20 °C
2.1: 95 percent / P-TsOH / CH2Cl2 / 1 h / 20 °C
3.1: 96 percent / NaOMe / methanol / 2 h / 20 °C
4.1: TFAA; DMSO; Et3N / CH2Cl2 / -78 °C
5.1: n-BuLi / tetrahydrofuran / -78 °C
6.1: 91 percent / AcOH; water / tetrahydrofuran / 1 h / 50 °C
7.1: 89 percent / NaH / dimethylformamide / 1 h / 20 °C
8.1: BH3*Me3S; NaOH; H2O2 / tetrahydrofuran / 24 h
8.2: oxalyl chloride; DMSO / CH2Cl2 / 4 h / -78 °C
9.1: 94 percent / Et3N / CH2Cl2 / 168 h / 20 °C
10.1: 92 percent / NaBH4 / ethanol; tetrahydrofuran / 0.17 h / 0 °C
11.1: 78 percent / NaH / dimethylformamide / 1 h / 20 °C
12.1: 66 percent / Cu(OTf)2; BH3*THF / 1 h
13.1: 86 percent / PPh3; I2; imidazole / toluene / 3 h / Heating
14.1: 60 percent / DBU / tetrahydrofuran / Heating
15.1: 93 percent / HgCl2 / acetone; H2O / 1 h / Heating
16.1: 53 percent / MsCl; DAMP / pyridine / 24 h / 20 °C
17.1: NaBH4; CeCl3*7H2O / ethanol; tetrahydrofuran / 0.17 h / -78 °C
18.1: 37 percent / Ph3P; DIAD / dioxane / 24 h / 20 °C
With
1H-imidazole; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; borane-THF; di-isopropyl azodicarboxylate; bisacodyl; water; dihydrogen peroxide; iodine; sodium methylate; copper(II) bis(trifluoromethanesulfonate); sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic anhydride; mercury dichloride;
In
tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene;
5.1: Wittig reaction / 15.1: Ferrier rearrangement / 18.1: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2007.03.031