Multi-step reaction with 17 steps
1.1: O3; NaHCO3 / CH2Cl2; methanol / -78 °C
1.2: 90 percent / Me2S / -78 - 20 °C
2.1: tetrahydrofuran; diethyl ether / -78 - -10 °C
3.1: 98 percent / KHMDS / tetrahydrofuran / -78 - 0 °C
4.1: aq. HF / acetonitrile / 20 °C
4.2: 87 percent / Et3N / CH2Cl2 / -78 - 20 °C
5.1: 92 percent / 2,6-di-tert-butyl-4-methylpyridine; BCl3 / CH2Cl2; heptane / 15 h / 20 °C
6.1: imidazole / acetonitrile
7.1: NaBH4 / methanol
8.1: Et3N / CH2Cl2
9.1: Na; naphthalene / 1,2-dimethoxy-ethane; tetrahydrofuran / -78 °C
10.1: NaBH3CN; AcOH / acetonitrile / 20 °C
11.1: 75 percent / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 7 h / Heating
12.1: 93 percent / H2 / Pd/C / ethyl acetate / 6 h / 20 °C
13.1: 83 percent / HCl / tetrahydrofuran; H2O / 20 °C
14.1: 89 percent / NaHMDS / dimethylformamide / 20 °C
15.1: 85 percent / tris(dimethylamino)sulfur (trimethylsilyl)difluoride / N,N-dimethyl-acetamide / 100 °C
16.1: 90 percent / KOH / ethanol / 90 °C
With
1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; 2,6-di-tert-butyl-4-methylpyridine; naphthalene; hydrogen fluoride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; hydrogen; sodium hexamethyldisilazane; sodium; boron trichloride; potassium hexamethylsilazane; sodium cyanoborohydride; sodium hydrogencarbonate; ozone; acetic acid; triethylamine;
palladium on activated charcoal; Grubbs catalyst first generation;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; n-heptane; dichloromethane; N,N-dimethyl acetamide; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
2.1: Grignarg reaction / 3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol050038m