Multi-step reaction with 12 steps
1.1: 95 percent / imidazole; 4-DMAP / CH2Cl2 / 12 h / 0 °C
2.1: 96 percent / DIBAL-H / CH2Cl2 / 1 h / -78 °C
3.1: (COCl)2; DMSO / CH2Cl2 / 1.5 h / -78 - -60 °C
3.2: 95 percent / Et3N / CH2Cl2 / -78 - -25 °C
4.1: 76 percent / diethyl ether / 1 h / 0 - 25 °C
5.1: 85 percent / pyridine; 4-DMAP / CH2Cl2 / 3 h / 0 °C
6.1: LDA / tetrahydrofuran / 0.17 h / -78 °C
6.2: TBSCl; HMPA / tetrahydrofuran / 24 h / -78 - 25 °C
7.1: diethyl ether / 0.5 h / 25 °C
8.1: 85 percent / HF*pyridine / pyridine; tetrahydrofuran / 2 h / 0 °C
9.1: (COCl)2; DMSO / CH2Cl2 / 1.5 h / -78 - -60 °C
9.2: 90 percent / Et3N / CH2Cl2 / -78 - -25 °C
10.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -78 °C
10.2: tetrahydrofuran / 0.5 h / -78 °C
11.1: Pd(OAc)2; DMSO / 72 h
11.2: NaBH4; CeCl3*7H2O / methanol / 1 h / -50 °C
11.3: pyridine; 4-DMAP / CH2Cl2 / 12 h / 0 - 25 °C
12.1: [Pd2dba3]*CHCl3; nBu3P; NaBH4 / dioxane; H2O / 12 h / 0 - 25 °C
With
pyridine; 1H-imidazole; dmap; palladium diacetate; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); oxalyl dichloride; tributylphosphine; potassium hexamethylsilazane; diisobutylaluminium hydride; pyridine hydrogenfluoride; dimethyl sulfoxide; lithium diisopropyl amide;
In
tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; water;
3.1: Swern oxidation / 6.1: Ireland-Claisen rearrangement / 9.1: Swern oxidation;
DOI:10.1002/anie.200460695