Multi-step reaction with 13 steps
1.1: 90 percent / imidazole / tetrahydrofuran / 1 h
2.1: t-BuLi / diethyl ether; pentane / 0.83 h / -78 - -45 °C
2.2: diethyl ether; pentane / 4 h / -45 - -20 °C
2.3: 58 percent / HMPA; n-BuLi / hexane; diethyl ether; tetrahydrofuran / 15 h / -20 °C
3.1: Hg(ClO4)2*4H2O / acetonitrile; H2O; CH2Cl2 / 0.17 h / 0 °C
3.2: 83 percent / HClO4 / acetonitrile; H2O; CH2Cl2 / 0.08 h
4.1: 90 percent / pyridine; 4-DMAP / CH2Cl2 / 13 h
5.1: 100 percent / 2,6-lutidine / CH2Cl2 / -78 - 0 °C
6.1: 98 percent / 2-methylcyclohexadiene; calcium carbonate / Pd(OH)2/C / ethanol / 5.5 h / 70 °C
7.1: 99 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0.33 h
8.1: 100 percent / NaClO2; NaH2PO4; 2-methyl-2-butene / ethyl-1-propenyl ether / H2O; tetrahydrofuran; 2-methyl-propan-2-ol / 6 h / 20 °C
9.1: 97 percent / Et3N / CH2Cl2; tetrahydrofuran / 0.5 h
10.1: 91 percent / DDQ / CH2Cl2; H2O / 2 h / 0 °C
11.1: 89 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 1 h
12.1: dicyclohexylboron chloride; triethylamine / pentane / -78 - 0 °C
12.2: pentane / 6.5 h / -78 °C
12.3: 64 percent / H2O2 / pentane; methanol / 1 h / 0 °C / pH 7
13.1: 88 percent / pyridine / CH2Cl2 / 24 h / 20 °C
With
pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; mercury(II) perchlorate; 2-methyl-but-2-ene; 2-methylcyclohexa-1,3-diene; dicyclohexylboron chloride; tert.-butyl lithium; Dess-Martin periodane; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; calcium carbonate;
palladium dihydroxide; ethyl-1-propenyl ether;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; pentane;
7.1: Dess-Martin oxidation / 11.1: Dess-Martin oxidation;
DOI:10.1021/ol017273z