Multi-step reaction with 13 steps
1: 85 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C
2: 65 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 3 h / -78 °C
3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C
4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C
5: 70 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C
6: 93 percent / H2O2; NaOH / methanol / 0 °C
7: 89 percent / CeCl3*7H2O; NaBH4 / methanol / 1 h / 0 - 20 °C
8: 100 percent / Et3N / tetrahydrofuran / 14 h / 0 - 20 °C
9: 90 percent / LiNEt2 / tetrahydrofuran / 2 h / Heating
10: Et3N / CH2Cl2 / 2 h / 0 °C
11: 63 percent / NaI; pyridine / acetone / 1 h / Heating
12: 90 percent / Bu4NF*3H2O / tetrahydrofuran / 14 h / 0 - 20 °C
13: 75 percent / pyridine; DMAP / 3 h / 0 °C
With
pyridine; 1H-imidazole; dmap; sodium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; lithium diethylamide; tetrabutyl ammonium fluoride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; diisopropylamine; sodium iodide;
In
tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination / 6: Epoxidation / 7: Reduction / 8: Substitution / 9: Rearrangement / 10: Acylation / 11: Elimination / 12: Hydrolysis / 13: Acylation;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T