Multi-step reaction with 13 steps
1.1: LiAlH4 / tetrahydrofuran / 43 h / Heating
2.1: 80 percent / pyridine / 24 h / 0 °C
3.1: 95 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating
4.1: 9-BBN / tetrahydrofuran / 48 h / Heating
4.2: 95 percent / 30 percent H2O2; 6 N aq. NaOH / ethanol / 1.5 h / 55 °C
5.1: 93 percent / imidazole; DMAP / dimethylformamide / 16 h / 20 °C
6.1: cyclohexene / 20 percent Pd(OH)2/C / ethanol / 6 h / Heating
7.1: 91 percent / pyridine / 19 h / 20 °C
8.1: NaH; DMSO / 0.75 h / 20 °C
8.2: 68 percent / dimethylsulfoxide / 0.75 h
9.1: 98 percent / TBAF / tetrahydrofuran / 10 h / 20 °C
10.1: 85 percent / PDC / CH2Cl2 / 22 h / 20 °C
11.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
11.2: 100 percent / tetrahydrofuran; hexane / 2 h / -78 °C
12.1: 100 percent / PPTS / CH2Cl2 / 1 h / 20 °C
13.1: 100 percent / TBAF / tetrahydrofuran / 14 h / 20 °C
With
pyridine; 1H-imidazole; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; cyclohexene;
palladium dihydroxide;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide;
1.1: Reduction / 2.1: Tosylation / 3.1: reductive cleavae / 4.1: hydroboration / 4.2: Oxidation / 5.1: silylation / 6.1: debenzylation / 7.1: Tosylation / 8.1: Metallation / 8.2: Substitution / 9.1: desilylation / 10.1: Oxidation / 11.1: Metallation / 11.2: Condensation / 12.1: acidolysis / 13.1: desilylation;
DOI:10.1021/jm980736v