Multi-step reaction with 10 steps
1.1: 100 percent / tosyl acid / 20 °C
2.1: BuLi / tetrahydrofuran / -15 - 0 °C
2.2: tetrahydrofuran / -10 °C
3.1: DDQ / CH2Cl2; H2O / 20 °C
4.1: K2CO3 / acetone / Heating
4.2: 81 percent / 185 °C
5.1: 93 percent / K2CO3 / acetone / Heating
6.1: m-CPBA / CH2Cl2 / 0 °C
6.2: 61 percent / Et3N / CH2Cl2; methanol / 20 °C
7.1: 88 percent / Et3N / CH2Cl2 / 20 °C
8.1: 90 percent / Billig ligand; H2; Rh(CO)2(acac) / toluene / 60 °C
9.1: 87 percent / SnCl2 / CH2Cl2 / 20 °C
10.1: 93 percent / K2CO3 / acetone / Heating
With
acetylacetonatodicarbonylrhodium(l); n-butyllithium; Billig ligand; hydrogen; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride;
In
tetrahydrofuran; dichloromethane; water; acetone; toluene;
4.2: Claisen rearrangement / 6.1: Baeyer-Villiger oxidation;
DOI:10.1016/j.tetlet.2004.11.148