Multi-step reaction with 8 steps
1.1: ozone; NaHCO3 / CH2Cl2 / -78 °C
1.2: 87 percent / acetic anhydride; pyridine / CH2Cl2 / Heating
2.1: 79 percent / BF3*Et2O / CH2Cl2 / 20 °C
3.1: 59 percent / H2 / Raney Ni / ethanol / 20 °C / 37503 Torr
4.1: 100 percent / sodium hydroxide / 20 °C
5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 20 °C
5.2: 65 percent / 4-(N,N-dimethylamino)pyridine / toluene / Heating
6.1: 59 percent / PhCH2OLi / tetrahydrofuran / 20 °C
7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 0 - 20 °C
7.2: 94 percent / 4-(N,N-dimethylamino)pyridine / toluene / 20 °C
8.1: 97 percent / HF / acetonitrile; H2O / 20 °C
With
sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; hydrogen fluoride; lithium benzyloxide; hydrogen; sodium hydrogencarbonate; ozone; triethylamine;
nickel;
In
tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
5.1: Yamaguchi lactonization / 7.1: Yamaguchi coupling;
DOI:10.1002/anie.200501511