Multi-step reaction with 10 steps
1.1: 91 percent / (Ph3P)4Pd; CuI; Et2NH / dimethylformamide / 9 h / 80 °C
2.1: 98 percent / H2 / Pd/C / ethanol; ethyl acetate / 12 h / 20 °C
3.1: 78 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C
4.2: 80 percent / tetrahydrofuran; hexane / 1.5 h / -78 °C
5.1: 95 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 0 °C
6.1: 88 percent / SmI2 / tetrahydrofuran / 0.25 h / -20 °C
7.1: 87 percent / HF*pyridine / tetrahydrofuran / 0.08 h / 0 °C
8.1: MnO2 / CH2Cl2 / 1 h / 20 °C
9.1: 1.57 g / 2-methyl-2-butene; NaH2PO4; aq. NaClO2 / 2-methyl-propan-2-ol / 1 h / 20 °C
10.1: aq. HCl / methanol / 72 h / 20 °C
With
hydrogenchloride; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; diethylamine; triethylamine;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;
3.1: Swern oxidation;
DOI:10.1021/ja042848j