Multi-step reaction with 23 steps
1.1: n-BuLi / tetrahydrofuran
2.1: Amberlyst-15E / methanol
3.1: Co2(CO)8; BF3*OEt2 / CH2Cl2
3.2: propargyl alcohol / 1,2-dichloro-ethane / 60 °C
4.1: Jones' reagent / acetone
4.2: 88 percent / PdCl2; CuCl / dimethylformamide; H2O
5.1: 86 percent / I(collidine)2PF6- / CH2Cl2
6.1: 90 percent / BF3*OEt2 / CH2Cl2
7.1: DIBAL-H / CH2Cl2
8.1: DBU / tetrahydrofuran
9.1: 81 percent / K2CO3 / methanol
10.1: 90 percent / BF3*OEt2 / CH2Cl2
11.1: p-nitro benzoic acid; DEAD; PPh3 / toluene
11.2: 94 percent / K2CO3 / methanol
12.1: PPTS / CH2Cl2
13.1: n-BuLi / tetrahydrofuran
14.1: Amberlyst-15E / methanol
15.1: Jones' reagent / acetone
16.1: I(collidine)2PF6 / CH2Cl2
17.1: BF3*OEt2 / CH2Cl2
18.1: DIBAL-H / CH2Cl2
19.1: DBU / tetrahydrofuran
20.1: 69 percent / n-BuLi
21.1: 65 percent / BF3*OEt2 / CH2Cl2
22.1: 83 percent / TBAF / tetrahydrofuran
With
n-butyllithium; jones' reagent; dicobalt octacarbonyl; Amberlyst-15E; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; bis(2,4,6-trimethylpyridine)iodine(I) hexafluorophosphate; diethylazodicarboxylate; 4-nitro-benzoic acid;
In
tetrahydrofuran; methanol; dichloromethane; acetone; toluene;
4.1: Wacker oxidation / 11.1: modified Mitsunobu inversion;
DOI:10.1016/S0040-4039(01)00286-6