Multi-step reaction with 14 steps
1.1: 97 percent / imidazole; DMAP / dimethylformamide / 60 °C
2.1: O3 / methanol / -78 °C
2.2: NaBH4 / methanol / 0 °C
3.1: imidazole; DMAP / CH2Cl2; dimethylformamide / 20 °C
4.1: aq. TsOH / acetone / 50 °C
5.1: hydrazine; TEA / ethanol / 100 °C
5.2: 93 percent / I2; DBU / diethyl ether / 0 - 20 °C
6.1: 100 percent / Cs2CO3; Pd(PPh3)4 / dimethylformamide / 50 °C
7.1: 100 percent / TBAF / tetrahydrofuran / 50 °C
8.1: 100 percent / H2 / [Ir(COD)Py(PCy3)]PF6 / CH2Cl2 / 20 °C
9.1: imidazole; DMAP / CH2Cl2; dimethylformamide / 20 °C
10.1: Dess-Martin periodinane / CH2Cl2 / 20 °C
11.1: TBAF / tetrahydrofuran / 20 °C
12.1: CBr4; PPh3 / CH2Cl2 / 0 - 20 °C
13.1: 91 percent / TsOH; CH(OEt)3 / CH2Cl2 / Heating
14.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran / -78 - -10 °C
14.2: 91 percent / diethyl ether; tetrahydrofuran / -78 - -30 °C
With
1H-imidazole; dmap; tetrakis(triphenylphosphine) palladium(0); carbon tetrabromide; TEA; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; thien-2-yl(cyano)copper lithium; orthoformic acid triethyl ester; triphenylphosphine; hydrazine;
Crabtree's catalyst;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
6.1: Suzuki-Miyaura coupling reaction / 10.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2007.01.024