Multi-step reaction with 12 steps
1.1: TFA / CH2Cl2 / 0 - 20 °C
1.2: 87 percent / NaOH / 0 °C
2.1: 79 percent / DMAP; TEA / CH2Cl2
3.1: 74 percent / BF3Et20 / tetrahydrofuran / -78 °C
4.1: 90 percent / Na2CO3 / benzene / 20 °C
5.1: 96 percent / Bu4NF / tetrahydrofuran / 20 °C
6.1: 93 percent / pyridine / 20 °C
7.1: 85 percent / OsO4; NaIO4 / tetrahydrofuran; H2O / 20 °C
8.1: pyrrolidine / toluene / Heating
8.2: 60 percent / ag. AcOH / 20 °C
9.1: tetrahydrofuran / 0 °C
10.1: 91 percent / MnO2 / CH2Cl2 / 20 °C
11.1: 99 percent / H2 / Lindlar catalyst / toluene / 20 °C
12.1: TFA / CH2Cl2 / 0 °C
12.2: 81 percent / ag. NaHCO3 / 20 °C
With
pyrrolidine; pyridine; dmap; manganese(IV) oxide; sodium periodate; osmium(VIII) oxide; TEA; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; trifluoroacetic acid;
Lindlar's catalyst;
In
tetrahydrofuran; dichloromethane; water; toluene; benzene;
3.1: Grignard reaction / 9.1: Grignard reaction / 12.2: intramolecular Michael addition;
DOI:10.1016/j.tetlet.2004.05.142