Multi-step reaction with 11 steps
1: 91 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C
2: 62 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / 3 h / -79 °C
3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C
4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C
5: 74 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C
6: 55 percent / CeCl3*7H2O; NaBH4 / methanol / 1 h / 0 - 20 °C
7: 99 percent / VO(acac)2; t-BuOOH / benzene; CH2Cl2 / 2 h / 0 - 5 °C
8: 100 percent / Et3N / tetrahydrofuran / 24 h / 0 - 20 °C
9: 95 percent / LiNEt2 / tetrahydrofuran / 2 h / Heating
10: 98 percent / pyridine / benzene / 2 h / -5 - 20 °C
11: 40 percent / P(OMe)3; maleinic anhydride / benzene / 24 h / Heating
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; cerium(III) chloride; oxalyl dichloride; bis(acetylacetonate)oxovanadium; lithium diethylamide; maleic anhydride; dimethyl sulfoxide; triethylamine; diisopropylamine; phosphorous acid trimethyl ester;
In
tetrahydrofuran; 2,4,6-trimethyl-pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination / 6: Reduction / 7: Epoxidation / 8: Substitution / 9: Rearrangement / 10: Acylation / 11: Elimination;
DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T