Multi-step reaction with 12 steps
1.1: 83 percent / ethyldiisopropylamine; KI / 1,2-dimethoxy-ethane / 3 h / Heating
2.1: 81 percent / trimethylamine oxide dihydrate; OsO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 5 h / 20 °C
3.1: aq. NaIO4 / diethyl ether / 3 h / 0 °C
4.1: NaH / toluene
4.2: 1.96 g / toluene / 2 h / 0 °C
5.1: H2 / Pd(OH)2/C / ethanol / 5 h / 20 °C / 760 Torr
6.1: 448 mg / EDCI*HCl / tetrahydrofuran / 4 h
7.1: 50 percent / NaH / dimethylformamide / 5.5 h / 20 °C
8.1: 86 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
9.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C
10.1: 18.6 mg / NaH / dimethylsulfoxide / 2 h / 20 °C
11.1: KH / dimethylformamide / 0.5 h / 0 °C
11.2: dimethylformamide / 3.5 h / 80 °C
12.1: 19.8 mg / Dess-Martin periodinane / CH2Cl2 / 2 h / 0 °C
With
sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; tetrabutyl ammonium fluoride; hydrogen; potassium hydride; sodium hydride; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium iodide;
palladium dihydroxide;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
4.2: Horner-Emmons reaction / 9.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation;
DOI:10.1021/jm0302086