Multi-step reaction with 12 steps
1.1: 100 percent / CeCl3; NaBH4 / methanol / 0.25 h / 0 °C
2.1: 93 percent / Ph3P; DEAD / CH2Cl2; tetrahydrofuran / 24.5 h / 0 - 4 °C
3.1: 91 percent / TMSCl; triethylamine; LiHMDS / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C
4.1: toluene; methanol / 20 °C
5.1: 80 percent / DIBAH / CH2Cl2 / 3.5 h / -78 °C
6.1: 18-crown-6-ether; KHMDS / tetrahydrofuran / 0.25 h / -78 °C
6.2: 88 percent / tetrahydrofuran / 6 h / -90 - -80 °C
7.1: DIBAH / CH2Cl2 / 5 h / -78 °C
8.1: 99 percent / NaHCO3; Dess-Martin periodinane / CH2Cl2 / 20 °C
9.1: 61 percent / hydroxylamine hydrochloride; polymer-supported 2,6-di-tert-butyl-pyridine / tetrahydrofuran / 24 h / 40 °C
10.1: 92 percent / NCS; pyridine / CHCl3 / 1.17 h / 40 - 60 °C
11.1: 77 percent / DDQ; phosphate buffer / CH2Cl2 / 2 h / pH 7 / sonication
12.1: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 16 h / 20 °C
With
pyridine; sodium tetrahydroborate; N-chloro-succinimide; chloro-trimethyl-silane; phosphate buffer; cerium(III) chloride; 18-crown-6 ether; hydroxylamine hydrochloride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
2.1: Mitsunobu reaction / 6.2: Still-Gennari olefination;
DOI:10.1016/j.tet.2007.02.126