Multi-step reaction with 18 steps
1.1: H2 / Pd(OH)2/C / ethyl acetate / 4 h
2.1: 77 percent / KH / tetrahydrofuran / 2 h / 35 °C
3.1: 100 percent / HMDS; TMSI / CH2Cl2 / 1 h / 0 °C
4.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
5.1: tetrahydrofuran / 0.5 h / 0 °C
6.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
7.1: NaHMDS / tetrahydrofuran / 0 °C
7.2: 298 mg / tetrahydrofuran / 1 h / 20 °C
8.1: 84 percent / DDQ; aq. NaHCO3 / CH2Cl2 / 1.5 h / 45 °C
9.1: KH / tetrahydrofuran / 1 h / 0 °C
10.1: 176 mg / (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 20 h / 20 °C
11.1: 95 percent / CSA / methanol; CH2Cl2 / 2.5 h / 0 °C
12.1: 95 percent / Bu3P / dimethylformamide / 4 h / 20 °C
13.1: NCS / CCl4; CH2Cl2 / 0.5 h / 20 °C
14.1: 30 percent / DTBMP; AgOTf; 4 Angstroem molecular sieves / CH2Cl2 / 2 h / -45 °C
15.1: TBAF / tetrahydrofuran / 20 h / 20 °C
16.1: CSA / CH2Cl2 / 1 h / 20 °C
16.2: HMDS; TMSI / CH2Cl2 / 1 h / 0 °C
16.3: AgOTf; 4 Angstroem molecular sieves / CH2Cl2; acetonitrile / 7 h / 30 °C
17.1: 83 percent / (PCy3)2Cl2Ru=CHPh / benzene / 5 h / 80 °C
18.1: 87 percent / KO2CN=NCOOK; pyridine; AcOH / methanol / 3 h / 20 °C
With
pyridine; N-chloro-succinimide; Grubbs catalyst first generation; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; trimethylsilyl iodide; tributylphosphine; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; potassium diazodicarboxylate; potassium hydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium dihydroxide;
In
tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;
4.1: Swern oxidation / 5.1: Grignard reaction / 6.1: Swern oxidation / 7.2: Wittig reaction;
DOI:10.1021/jo0603025