Multi-step reaction with 17 steps
1.1: 99 percent / H2 / Raney-Ni / ethanol / 1 h / 25 °C
2.1: 88 percent / H2 / Pd(OH)2/C / ethanol / 3 h / 25 °C
3.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / 0 - 25 °C
4.1: Mg / tetrahydrofuran / 2 h / 25 °C
4.2: tetrahydrofuran / 2 h / -78 - 0 °C
5.1: 40.9 g / Dess-Martin periodinane / CH2Cl2 / 4 h / 0 - 25 °C
6.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C
7.1: 96 percent / TBAF / tetrahydrofuran / 48 h / 25 °C
8.1: 97 percent / Et3N; 4-DMAP / CH2Cl2 / 16 h / 0 - 25 °C
9.1: 98 percent / imidazole; 4-DMAP / CH2Cl2 / 0.5 h / 0 °C
10.1: N-methylmorpholine-N-oxide; OsO4 / 2-methyl-propan-2-ol; H2O; tetrahydrofuran / 12 h / 25 °C
11.1: 41.5 g / NaIO4 / 2-methyl-propan-2-ol; H2O; various solvents / 5 h / 20 °C / pH 7
12.1: n-BuLi / toluene; tetrahydrofuran / 3 h / -30 °C
12.2: tetrahydrofuran; toluene / 1 h / -30 °C
13.1: 13.2 g / Dess-Martin periodinane; pyridine / CH2Cl2 / 2 h / 0 °C
14.1: 70 percent / TMSOTf / CH2Cl2 / 3 h / -78 - -30 °C
15.1: 95 percent / 4-DMAP; pyridine / CH2Cl2 / 3 h / 0 - 25 °C
16.1: 91 percent / 2,6-lutidine; N-bromosuccinimide; H2O / acetonitrile / 2 h / 25 °C
17.1: 92 percent / NaBH4 / methanol / 0.08 h / -5 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; water; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester;
palladium dihydroxide; nickel;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; various solvents; water; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja054750q