Multi-step reaction with 19 steps
1.1: 98 percent / CSA / CH2Cl2 / 0 - 20 °C
2.1: 78 percent / Li; liq. NH3 / tetrahydrofuran / 0.17 h / -33 °C
3.1: 70 percent / Et3N; DMAP / CH2Cl2 / 0 - 20 °C
4.1: 92 percent / TBAF / tetrahydrofuran / 0 - 20 °C
5.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 2 h / -78 - 0 °C
6.1: CH2Cl2 / 20 °C
7.1: 86 percent / LiBH4 / tetrahydrofuran / 16 h / 0 - 20 °C
8.1: 96 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 0 - 20 °C
9.1: 65 percent / TFA / 2-methyl-propan-2-ol / 2 h / 20 °C
10.1: 100 percent / 2,6-lutidine / 0.17 h / 0 °C
11.1: 75 percent / HF; pyridine / tetrahydrofuran / 5 h / 0 - 20 °C
12.1: SO3; pyridine; DMSO / CH2Cl2 / 0.5 h / 0 - 20 °C
13.1: CH2Cl2 / 20 °C
14.1: 100 percent / DIBAL-H / CH2Cl2 / 0.25 h / -78 °C
15.1: SO3; pyridine; DMSO / CH2Cl2 / 0.5 h / 0 - 20 °C
16.1: Ph3P / CH2Cl2 / 0.5 h / 0 °C
16.2: EtMgBr / tetrahydrofuran / 1 h / -78 - 0 °C
17.1: 72 percent / nBuLi / tetrahydrofuran / -78 - 20 °C
18.1: 100 percent / Et3N; DMAP / CH2Cl2 / 0.08 h / 0 °C
19.1: Bu3SnH / Pd(Ph3P)2Cl2 / tetrahydrofuran / 0.5 h / 20 °C
19.2: I2 / CH2Cl2 / 0.5 h / -78 - 0 °C
With
pyridine; 2,6-dimethylpyridine; dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; hydrogen fluoride; sulfur trioxide; tetrabutyl ammonium fluoride; ammonia; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; lithium; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid;
bis-triphenylphosphine-palladium(II) chloride;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2007.04.016