Multi-step reaction with 14 steps
1.1: 79 percent / LiN(TMS)2 / tetrahydrofuran / 0.17 h / -78 - 20 °C
2.1: 64 percent / BF3*Et2O / toluene / 12 h / 20 °C
3.1: LiN(TMS)2 / tetrahydrofuran / 0.08 h / 20 °C
3.2: 68 percent / 30 percent H2O2; aq. NaHCO3 / CH2Cl2 / 36 h / 20 °C
4.1: 81 percent / NaBH4; CeCl3*7H2O; NaOEt / ethanol / 12 h / 0 - 40 °C
5.1: 86 percent / (COCl)2; Et3N / dimethylsulfoxide; CH2Cl2 / 1 h / -78 - 20 °C
6.1: 81 percent / tetrahydrofuran / 1 h / -10 °C
7.1: 84 percent / o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 3 h / 20 °C
8.1: 85 percent / diisopinocampheylchloroborane; Et3N / CH2Cl2 / 4 h / -78 - 20 °C
9.1: 75 percent / TMSOTf / CH2Cl2; cyclohexane / 2 h / 20 °C
10.1: 75 percent / TMSOTf / CH2Cl2 / 1 h / -78 - 0 °C
11.1: LiN(TMS)2 / tetrahydrofuran / 2 h / -78 - 60 °C
11.2: 64 percent / BnOMe / Pd-C / toluene / 15 h / 110 °C
12.1: 85 percent / t-BuOK / H2O; 2-methyl-propan-2-ol / 0.25 h / 60 °C
13.1: 90 percent / H2 / Pd(OH)2-C / dioxane / 2 h / 20 °C
14.1: 76 percent / LiBF4 / tetrahydrofuran; acetonitrile; H2O / 72 h / 70 °C
With
sodium tetrahydroborate; lithium tetrafluoroborate; cerium(III) chloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; diisopinocamphenylchloroborane; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; sodium ethanolate; triethylamine; lithium hexamethyldisilazane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
palladium hydroxide - carbon;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; cyclohexane; water; dimethyl sulfoxide; toluene; acetonitrile; tert-butyl alcohol;
6.1: Grignard reaction;
DOI:10.7164/antibiotics.55.1076