Multi-step reaction with 20 steps
1.1: 72 percent / SnCl4 / CH2Cl2 / 8 h / 0 - 25 °C
2.1: 92 percent / Raney Ni / methanol / 3 h / Heating
3.1: 92 percent / LiAlH4 / diethyl ether / 12 h / 25 °C
4.1: 84 percent / imidazole; DMAP / CH2Cl2 / 8 h / 25 °C
5.1: 89 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 25 °C
6.1: toluene / 1 h / -78 °C
6.2: NaH / tetrahydrofuran / 1 h / 0 °C
6.3: TBAI / tetrahydrofuran / 12 h / 25 °C
7.1: 93 percent / TBAF / tetrahydrofuran / 12 h / 25 °C
8.1: 93 percent / iPr2NEt / CH2Cl2 / 8 h / 0 - 25 °C
9.1: OsO4; NMO; pyridine / acetone; H2O / 12 h / 25 °C
9.2: 91 percent / NaIO4 / tetrahydrofuran; H2O / 2 h / 25 °C
10.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C
10.2: 77 percent / tetrahydrofuran / 2 h / -78 °C
11.1: 98 percent / TBAF / tetrahydrofuran / 0.5 h / 25 °C
12.1: 91 percent / DDQ / CH2Cl2 / 1 h / 25 °C / pH 7.0
13.1: 93 percent / imidazole; DMAP / CH2Cl2 / 8 h / 40 °C
14.1: n-BuLi / hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 0.5 h / -78 °C
14.2: hexane; tetrahydrofuran; 1,2-dimethoxy-ethane / 1 h / -78 °C
15.1: Ph2S / sunlight
16.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
17.1: 89 percent / DDQ / H2O; CH2Cl2 / 0.5 h / 25 °C / pH 7.0
18.1: 94 percent / TEMPO; bis(acetoxy)iodobenzene / CH2Cl2 / 2 h / 25 °C
19.1: BF3*OEt2 / tetrahydrofuran / 1 h / -78 °C
20.1: 86 percent / iPr2NEt / CH2Cl2 / 12 h / 25 °C
With
pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; [bis(acetoxy)iodo]benzene; diphenyl sulfide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tin(IV) chloride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
nickel;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; hexane; dichloromethane; water; acetone; toluene;
5.1: Dess-Martin oxidation / 16.1: Dess-Martin oxidation / 19.1: Mukaiyama reaction;
DOI:10.1002/anie.200460203
