Multi-step reaction with 9 steps
1: 93 percent / LiAlH4 / diethyl ether / 20 h / -78 deg C to r.t.
2: 86 percent / 50percent aq. NaOH, p-toluenesulfonyl chloride / benzyltriethylammonium chloride (TEBA) / CH2Cl2 / 2 h / 0 deg C to r.t.
3: 1. n-butyllithium / 1. hexane, THF, r.t., 1 h; 2. THF, 0 deg C to r.t., 20 h
4: 88 percent / CH2Cl2 / 14 h / 0 deg C to r.t.
5: 1. OsO4, N-methylmorpholine-N-oxide; 2. Na2SO3 / 1. t-butanol, diethyl ether, water, acetone, r.t., 3 d; 2. water, 30 min
6: 80 percent / Pb(OAc)4, CaCO3 / CH2Cl2 / 0.75 h / Ambient temperature
7: 1. n-butyllithium / 1. THF, hexane, -78 deg C, 1 h; 2. THF, -78 deg C, 20 h
8: 53 percent / citric acid / methanol; H2O / 25 h / Ambient temperature
9: p-toluenesulfonyl chloride, pyridine / 20 h / Ambient temperature
With
pyridine; lead(IV) acetate; sodium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 4-methylmorpholine N-oxide; p-toluenesulfonyl chloride; citric acid; calcium carbonate; sodium sulfite;
N-benzyl-N,N,N-triethylammonium chloride;
In
methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4020(01)96205-2