Multi-step reaction with 18 steps
1.1: NaH / dimethylformamide / -20 - 20 °C
2.1: 6.24 g / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C
4.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5.1: H2O; NMO; OsO4 / acetone / 4 h / 20 °C
6.1: 533 mg / NaIO4; H2O / methanol / 2 h / 0 °C
7.1: 73 percent / benzene / 48 h / 80 °C
8.1: 84 percent / benzene / 39 h / 70 °C
9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
10.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
13.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
13.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
14.1: DMAP / pentane / 168 h / 20 °C
14.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
15.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
16.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
17.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
With
pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene;
2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation;
DOI:10.1021/jo062089i