Multi-step reaction with 20 steps
1: 99 percent / 1 M HCl / H2O; tetrahydrofuran
2: acetonitrile
3: NaOMe / methanol
4: 42 percent / imidazole
5: 100 percent / LiAlH4 / tetrahydrofuran
6: pyridine
7: LiBr / dimethylformamide
8: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide
9: 45 percent / H2O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C
10: 80 percent / AcOH / tetrahydrofuran; H2O
11: Dess-Martin periodinane / CH2Cl2
12: KHMDS; 18-crown-6 / tetrahydrofuran; toluene
13: 100 percent / DIBAL / toluene
14: Dess-Martin periodinane / CH2Cl2
15: t-BuMgCl / tetrahydrofuran
16: 86 percent / Al-Hg / tetrahydrofuran; H2O
17: 99 percent / pyridine
18: 93 percent / HF / pyridine; tetrahydrofuran
19: 90 percent / TMSOTf; 2,6-lutidine / CH2Cl2
20: DMAP; Et3N / CH2Cl2
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; N-chloro-succinimide; lithium aluminium tetrahydride; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; aluminium amalgam; hydrogen fluoride; tert-butylmagnesium chloride; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; lithium bromide;
In
tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
2: Wittig reaction / 11: Dess-Martin oxidation / 12: Still-modified Horner-Emmons reaction / 14: Dess-Martin oxidation;
DOI:10.1021/ol0341804