Multi-step reaction with 14 steps
1.1: H2 / Pd/C / ethyl acetate / 20 h / 20 °C / 760.05 Torr
2.1: PPTS / benzene / 3.5 h / Heating
3.1: 5.18 g / Na; liq.NH3 / tetrahydrofuran; liquid ammonia / 0.5 h / -78 °C
4.1: NaH / dimethylformamide; various solvent(s) / 3 h / 0 °C
4.2: dimethylformamide; various solvent(s) / 4 h / 0 °C
5.1: 104.3 mg / aq. HCl / acetone / 18 h / 50 °C
6.1: (Me3Si)2NH / CH2Cl2 / 0.5 h / 20 °C
6.2: CH2Cl2 / 2 h / 20 °C
7.1: AIBN; tributylstannane / benzene / 4.5 h / 80 °C
7.2: 10.8 mg / aq. HCl / methanol / 2 h / 20 °C
8.1: NaH; Bu4NI / dimethylformamide; various solvent(s) / 6 h / 20 °C
9.1: OsO4; pyridine / 2-methyl-propan-2-ol; tetrahydrofuran; H2O / 0.5 h / 20 °C
9.2: 433.2 mg / NaIO4 / H2O; 2-methyl-propan-2-ol; tetrahydrofuran / 6 h / 20 °C
10.1: KHMDS / tetrahydrofuran / 0.25 h / -50 °C
10.2: tetrahydrofuran / 0.67 h / -78 °C
11.1: 20.1 mg / ZnCl2*OEt2 / diethyl ether; CH2Cl2 / 16 h / -25 °C
12.1: 85 percent / SmI2; water / tetrahydrofuran / 0.08 h / 20 °C
13.1: 28 percent / LiAlH4 / tetrahydrofuran / 22 h / -78 - 20 °C
14.1: 99 percent / H2 / Pd(OH)2/C / methanol / 3 h / 20 °C / 760.05 Torr
With
pyridine; hydrogenchloride; osmium(VIII) oxide; lithium aluminium tetrahydride; samarium diiodide; zinc chloride diethyl ether; 2,2'-azobis(isobutyronitrile); ammonia; water; hydrogen; tri-n-butyl-tin hydride; sodium; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane;
palladium dihydroxide; palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ammonia; water; ethyl acetate; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;
DOI:10.1021/ol0161514