Multi-step reaction with 18 steps
1.1: 98 percent / KH / tetrahydrofuran / Heating
2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating
3.1: aq. HCl / tetrahydrofuran / 3 h / Heating
4.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C
5.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C
5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C
6.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C
7.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C
8.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C
9.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C
10.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C
11.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C
12.1: NaBH4 / methanol / 5 h / 20 °C
13.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating
14.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C
15.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C
16.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C
17.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C
18.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating
With
1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(O-isopropoxyphenylmethylene)ruthenium; ammonium heptamolybdate; sodium tetrahydroborate; rhodium(III) chloride; selenium(IV) oxide; bis(acetylacetonate)oxovanadium; potassium tert-butylate; dihydrogen peroxide; iodine; oxygen; pyridinium p-toluenesulfonate; potassium hydride; lithium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorous acid trimethyl ester;
In
tetrahydrofuran; methanol; decane; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene;
2.1: Grubbs reaction;
DOI:10.1021/ja044123l