Multi-step reaction with 16 steps
1.1: LiAlH4 / diethyl ether / 1 h / 0 °C
2.1: 1.56 g / 2,6-lutidine / CH2Cl2 / 2 h / Heating
3.1: 100 percent / H2 / Pd(OH)2-C / ethyl acetate / 49 h
4.1: 599 mg / Et3N / CH2Cl2 / 3 h / Heating
5.1: 95 percent / CuBr / tetrahydrofuran; diethyl ether / 1 h / -20 - 20 °C
6.1: O3(g) / methanol; CH2Cl2 / -78 °C
6.2: Me2S; NaBH4 / methanol; CH2Cl2 / 1 h / 0 °C
7.1: 2.13 g / pyridine / CH2Cl2 / 20 °C
8.1: O3(g) / methanol; CH2Cl2 / -78 °C
8.2: NaBH4 / methanol; CH2Cl2 / 1 h / 20 °C
9.1: CSA / CH2Cl2 / 1 h / 0 °C
10.1: 2.03 g / aq. AcOH / tetrahydrofuran / 3 h / 30 °C
11.1: 2-nitrophenyl selenocyanate; Bu3P / tetrahydrofuran / 0.5 h / 20 °C
11.2: 97 percent / NaHCO3; aq. H2O2 / tetrahydrofuran / 1 h / 40 °C
12.1: 100 percent / TBAF / tetrahydrofuran / 14 h / Heating
13.1: Et3N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 40 °C
13.2: 90 percent / DMAP / toluene / 0.5 h / 40 °C
14.1: 99 percent / TBAF / tetrahydrofuran / 3 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; tributylphosphine; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; ozone; acetic acid; triethylamine; copper(I) bromide;
palladium hydroxide - carbon;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1021/ja036984k