Multi-step reaction with 31 steps
1.1: NaH / tetrahydrofuran / 0 °C
2.1: 96 percent / D2O; CH2Cl2 / -30 - -10 °C
3.1: imidazole; 4-(dimethylamino)pyridine / CH2Cl2 / 20 °C
4.1: diisobutylaluminum hydride / tetrahydrofuran / 0 °C
5.1: 88 percent / 3-chloroperoxybenzoic acid / CH2Cl2 / 0 °C
6.1: pyridinium dichromate; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 60 °C
7.1: 0 °C
8.1: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C
9.1: 90 percent / D2O; CH2Cl2 / -30 - -10 °C
10.1: 93 percent / 2,6-lutidine / CH2Cl2 / 0 °C
11.1: 98 percent / diisobutylaluminum hydride / tetrahydrofuran / 0 °C
12.1: 98 percent / imidazole; DMAP / CH2Cl2 / 0 °C
13.1: 99 percent / lithium di-tert-butylbiphenylide / tetrahydrofuran / -78 - -45 °C
14.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 20 °C
15.1: ZnI2 / 20 °C
16.1: tetrahydrofuran / -78 °C
17.1: aq. HF / acetonitrile / 20 °C
18.1: pyridine / CH2Cl2 / 0 °C
19.1: Dess-Martin periodinane; pyridine / H2O; CH2Cl2 / 20 °C
20.1: potassium hexamethyldisilazide / tetrahydrofuran / -78 °C
20.2: 94 percent / Et2Zn / diethyl ether / Heating
21.1: 94 percent / FeCl3; pyridine / dimethylformamide / 100 °C
22.1: tetrahydrofuran / -78 °C
22.2: MeLi / tetrahydrofuran
22.3: 92 percent / aq. HF / acetonitrile / 20 °C
23.1: MnO2 / CH2Cl2 / 20 °C
24.1: NaH / tetrahydrofuran / 20 °C
25.1: 69 percent / tetrabutylammonium tribromide; 2,6-lutidine / 1,2-dichloro-ethane / 20 °C
26.1: 97 percent / dimethylformamide / 20 °C
27.1: K2CO3 / methanol / 0 °C
27.2: 98 percent / NaH / tetrahydrofuran / 20 °C
28.1: 92 percent / aq. NaOH / methanol / 20 °C
29.1: SOCl2
30.1: NaH / tetrahydrofuran / 20 °C
31.1: 95 percent / silver trifluoroacetate; Et3N; molecular sieves 4 Angstroem / tetrahydrofuran / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; manganese(IV) oxide; sodium hydroxide; dipyridinium dichromate; thionyl chloride; 4 A molecular sieve; lithium di-tert-butylbiphenylide; hydrogen fluoride; tetrabutyl ammonium fluoride; silver trifluoroacetate; tetra-N-butylammonium tribromide; iron(III) chloride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide;
In
tetrahydrofuran; methanol; dichloromethane; water; water-d2; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
1.1: Horner-Wadsworth-Emmons reaction / 7.1: Wittig reaction / 24.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/anie.200462300