Multi-step reaction with 15 steps
1.1: 75 percent / H2 / Pd/C / ethanol / 24 h / 2068.65 Torr
2.1: dimethyl sulfoxide; oxalyl chloride; ethyldiisopropylamine / CH2Cl2 / 0.92 h / -78 - 20 °C
3.1: 3.39 g / toluene / 1 h / 70 °C
4.1: sodium hexamethyldisilazide / tetrahydrofuran / 0 - 20 °C
4.2: 82 percent / tetrahydrofuran / 0.58 h / -78 - 20 °C
5.1: 73 percent / diisobutylaluminum hydride / CH2Cl2; hexane / -78 - 0 °C
6.1: triethylamine / CH2Cl2 / 0 - 20 °C
7.1: 3.53 g / sodium iodide / acetone / 2 h / Heating
8.1: 98 percent / benzene / 14 h / Heating
9.1: sodium hexamethyldisilazide / tetrahydrofuran / 1 h / -78 °C
9.2: 78 percent / tetrahydrofuran / -78 - 20 °C
10.1: 90 mg / benzene; CH2Cl2 / 120 h / 20 °C
11.1: 99 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0.08 h / -78 °C
12.1: triethylamine / CH2Cl2 / 0 - 20 °C
13.1: 126 mg / sodium iodide / acetone / 1 h / Heating
14.1: hydrazine monohydrate; 1-hexene / ethanol / 1 h / 40 °C
15.1: 19 mg / air; 1-hexene / CH2Cl2 / 3 h
With
1-hexene; oxalyl dichloride; air; hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; hydrazine hydrate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide;
palladium on activated charcoal;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; acetone; toluene; benzene;
2.1: Swern oxidation / 3.1: Wittig olefination / 4.2: Wittig olefination / 10.1: Wittig olefination;
DOI:10.1021/ol990281j