Multi-step reaction with 16 steps
1.1: Et2BOMe / tetrahydrofuran; methanol / 0.67 h / -78 °C
1.2: 85 percent / NaBH4 / tetrahydrofuran; methanol / 7.17 h / -78 °C
2.1: 60 percent / DDQ; molecular sieves 4 Angstroem / CH2Cl2 / 2 h / 0 - 20 °C
3.1: 99 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / -78 - 0 °C
4.1: 41 percent / DIBALH / CH2Cl2; hexane / 12.5 h / -78 - -45 °C
5.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 1.17 h / 0 °C
6.1: CrCl2 / tetrahydrofuran / 17 h / 20 °C
7.1: 1.85 g / NaH / tetrahydrofuran / 1.3 h / 0 - 20 °C
8.1: 75 percent / HF*pyridine; pyridine / tetrahydrofuran / 6 h / 0 - 20 °C
9.1: 93 percent / triphenylphosphine; imidazole; I2 / benzene; diethyl ether / 0.67 h / 20 °C
10.1: 78 percent / triphenylphosphine / benzene / 16 h / 20 - 80 °C
11.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0 - 20 °C
11.2: 82 percent / tetrahydrofuran / -78 - 20 °C
12.1: tert-butyllithium / diethyl ether; pentane / 0.33 h / -78 °C
12.2: 43 percent / diethyl ether; pentane / 1.17 h / -78 - -10 °C
13.1: 100 percent / 2,6-lutidine / CH2Cl2 / 1.5 h / -78 - 0 °C
14.1: 60 percent / HF*pyridine; pyridine / tetrahydrofuran / 14 h / 0 °C
15.1: Dess-Martin periodinane / CH2Cl2 / 1 h / 0 - 20 °C
16.1: NaH2PO4*H2O; NaClO2 / H2O; tetrahydrofuran; 2-methyl-propan-2-ol
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; sodium chlorite; sodium dihydrogenphosphate; pyridine-SO3 complex; 4 A molecular sieve; diethyl methoxy borane; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; tert-butyl alcohol; pentane; benzene;
6.1: Nozaki-Hiyama-Kishi reaction / 7.1: Peterson elimination / 15.1: Dess-Martin oxidation;
DOI:10.1021/jm061385k