Multi-step reaction with 11 steps
1: 74 percent / LiAlH4 / diethyl ether / -78 °C
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 35 min, 2.) CH2Cl2, -78 deg C, 15 min
3: 1.) MeLi-LiBr / 1.) THF, -78 deg C, 2.) THF, -78 deg C, 3.5 h
4: I2 / benzene / 2 h / 25 °C
5: 72 percent / K2CO3 / methanol
6: 87 percent / 2,6-lutidine / CH2Cl2
7: 62 percent / Pr4NRuO4, NMO / CH2Cl2 / 25 °C
8: 74 percent / NaClO2, Na2HPO4, 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 25 °C
9: 83 percent / n-Bu4NF / tetrahydrofuran
10: 57 percent / DCC, DMAP, HCl / CHCl3 / 70 °C
11: 90 percent / m-CPBA / CH2Cl2 / -78 °C
With
2,6-dimethylpyridine; hydrogenchloride; dmap; sodium chlorite; disodium hydrogenphosphate; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; methyllithium; iodine; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; lithium bromide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; water; tert-butyl alcohol; benzene;
DOI:10.1021/ja961071u