Multi-step reaction with 23 steps
1: diethyl ether / Ambient temperature
2: Et3N / DMAP / CH2Cl2 / Ambient temperature
4: DEAD-Ph3P / CH2Cl2 / Ambient temperature
5: H2 / Pd/C / methanol
6: Et3N / CH2Cl2 / -10 °C
7: MeONa / methanol / Ambient temperature
8: diethyl ether / Ambient temperature
9: H2 / Pd/C / methanol
10: H(1+)
11: pyridine
12: Swern oxidation
13: MeLi / tetrahydrofuran / -78 °C
14: methylaluminum bis-(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR) / CH2Cl2 / -78 °C
15: NaBH4 / 0.25 h / -20 °C
16: 92 percent / MsCl, Et3N, DMAP / CH2Cl2
17: Bu4NF / tetrahydrofuran
18: Bu3P / tetrahydrofuran / 1 h / Ambient temperature
19: 1.) NaIO4; 2.) Et3N / 1.) MeOH; 2.) PhCH3, reflux
20: 86 percent / Hg(OTFA)2 / H2O; acetone / 1 h / slow addition of the substrate to catalyst
21: 93 percent / MsCl, Et3N / CH2Cl2 / -10 deg C up to RT
22: CeCl3*7H2O, NaBH4 / methanol
23: 98 percent / DMAP/pyridine
With
pyridine; dmap; sodium tetrahydroborate; sodium periodate; cerium(III) chloride; tributylphosphine; tetrabutyl ammonium fluoride; methyllithium; hydrogen; sodium methylate; hydrogen cation; methanesulfonyl chloride; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; diethylazodicarboxylate;
dmap; palladium on activated charcoal; mercury(II) trifluoroacetate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(00)75797-2