Multi-step reaction with 14 steps
1.1: LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 °C
1.2: 15.7 g / acetonitrile / 1 h / 20 °C
2.1: 96 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - -60 °C
3.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH2Cl2 / 10 h / -20 °C
4.1: 88 percent / PPh3; CCl4; NaHCO3 / 3 h / Heating
5.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C
6.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C
7.1: O3; 2,6-lutidine / methanol / 2 h / -78 °C
7.2: Me2S / methanol / 1 h / 20 °C
8.1: iPr2NLi / tetrahydrofuran; hexane / 1 h / -78 °C
8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C
9.1: 8.42 g / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
10.1: imidazole / dimethylformamide / 1 h / 20 °C
11.1: (COCl)2; DMSO; Et3N / CH2Cl2 / 0.5 h
12.1: 7.68 g / tetrahydrofuran / 1 h / -78 °C
13.1: 91 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
14.1: O3; 2,6-lutidine / methanol; propan-2-ol / 5 h / -78 °C
14.2: Me2S / methanol; propan-2-ol / 1 h / 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide;
titanium(IV) isopropylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;
1.2: Horner-Wadsworth-Emmons reaction / 3.1: Sharpless asymmetric epoxidation / 11.1: Swern oxidation;
DOI:10.1002/anie.200600458