Multi-step reaction with 16 steps
1.1: 96 percent / NaH / 1,2-dimethoxy-ethane; various solvent(s) / 6 h / Heating
2.1: 99 percent / DIBAL-H / tetrahydrofuran; hexane / 0.5 h / 0 °C
3.1: 81 percent / Hg(OAc)2 / 24 h / Heating
4.1: 81 percent / triisobutylaluminum / CH2Cl2; hexane / 1 h / 20 °C
5.1: 14.35 g / n-Bu3P / tetrahydrofuran / 14 h / 20 °C
6.1: 91 percent / H2O2 / tetrahydrofuran / 1 h / 20 °C
7.1: 100 percent / aq. HCl / ethanol / 2 h / 20 °C
8.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.5 h / 20 °C
9.1: 89 percent / benzene / 5 h / Heating
10.1: 100 percent / DIBAl-H / tetrahydrofuran; hexane / 0.5 h / 0 °C
11.1: 92 percent / L-(+)-DIPT; molecular sieves 4 Angstroem; TBHP / Ti(i-PrO)4 / CH2Cl2 / -25 - 20 °C
12.1: 95 percent / triphenylphosphine; I2; imidazole / benzene / 0.5 h / 20 °C
13.1: 96 percent / Zn; acetic acid / 0.5 h / 50 °C
14.1: 98 percent / Et3N / CH2Cl2 / 0.5 h / 20 °C
15.1: (PCy3)2Cl2Ru=CHPh / CH2Cl2 / 48 h / 20 °C
15.2: 87 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C / Acid hydrolysis
16.1: 94 percent / TBAF / tetrahydrofuran / 6 h / 20 °C
With
1H-imidazole; hydrogenchloride; tert.-butylhydroperoxide; Grubbs catalyst first generation; oxalyl dichloride; L-(+)-diisopropyl tartrate; tributylphosphine; 4 A molecular sieve; mercury(II) diacetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; triisobutylaluminum; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc;
titanium(IV) isopropylate;
In
tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; benzene;
1.1: Horner-Emmons reaction / 9.1: Wittig reaction / 11.1: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/ol034020s