Multi-step reaction with 15 steps
1.1: lithium diisopropylamide / tetrahydrofuran / 0.08 h / -78 °C
1.2: trimethylchlorosilane / tetrahydrofuran / 3 h / Heating
1.3: 63 percent / methanol / 0.17 h / 20 °C
2.1: 97 percent / diethyl ether
3.1: 89 percent / DIBAL-H / toluene / 1 h / 20 °C
4.1: 92 percent / pyridine
5.1: 85 percent / dimethylsulfoxide / 2 h / 80 °C
6.1: 81 percent / 20percent KOH / bis-(2-hydroxy-ethyl) ether / 1 h / Heating
7.1: 98 percent / diethyl ether
8.1: 84 percent / DIBAL-H / toluene / 1 h / 20 °C
9.1: 98 percent / pyridine
10.1: 68 percent / ozone; triphenylphosphane / CH2Cl2; methanol
11.1: hydroxylamine hydrochloride; sodium acetate / ethanol
12.1: 1.52 g / sodium acetate / acetic anhydride / Heating
13.1: potassium hydroxide / methanol / 2 h / Heating
14.1: 95 percent / triphenylphosphane / CCl4 / 2 h / Heating
15.1: 91 percent / 1 h / 130 °C
With
pyridine; potassium hydroxide; hydroxylamine hydrochloride; sodium acetate; diisobutylaluminium hydride; ozone; triphenylphosphine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; dichloromethane; acetic anhydride; dimethyl sulfoxide; toluene; diethylene glycol;
1.1: Ireland rearrangement;
DOI:10.1002/1099-0690(200104)2001:7<1349::AID-EJOC1349>3.0.CO;2-9