Multi-step reaction with 16 steps
1.1: 93 percent / imidazole / dimethylformamide / 20 °C
2.1: NaH; 15-crown-5 / tetrahydrofuran / 0.5 h / 0 °C
2.2: 96 percent / tetrahydrofuran / 20 °C
3.1: 93 percent / TBAF / tetrahydrofuran / 20 °C
4.1: 91 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
5.1: 95 percent / oxone / dimethylformamide / 0 °C
6.1: ClCO2Et; Et3N / tetrahydrofuran / 0.5 h / 0 °C
6.2: 85 percent / tetrahydrofuran; diethyl ether / 20 °C
7.1: 80 percent / copper(II) hexafluoroacetylacetonate / tetrahydrofuran; CH2Cl2 / 4 h / Heating
8.1: 98 percent / NaBH4 / ethanol / 20 °C
9.1: 97 percent / imidazole / dimethylformamide / 20 °C
10.1: N-methylmorpholine N-oxide; aq. OsO4 / tetrahydrofuran / 1.5 h / 20 °C
11.1: 240 mg / aq. NaIO4 / tetrahydrofuran / 20 °C
12.1: 99 percent / NaBH4 / ethanol / 20 °C
13.1: 97 percent / TBAF / tetrahydrofuran / 20 °C
14.1: 91 percent / imidazole / dimethylformamide / 0.17 h / 20 °C
15.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 20 °C
16.1: lithium hexamethyldisilazide / tetrahydrofuran / 1.5 h / -80 °C
16.2: tetrahydrofuran / 28 h / 0 °C
With
1H-imidazole; Oxone; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; copper(II) hexafluoro-2,4-pentanedionate; 15-crown-5; tetrabutyl ammonium fluoride; chloroformic acid ethyl ester; sodium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.53.989