Multi-step reaction with 16 steps
1: 98 percent / H2 / Pd/C / ethyl acetate / 12 h / 760.05 Torr
2: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
3: 84 percent / Jones reagent / acetone / 0.5 h / 20 °C
4: 78 percent / SmI2; MeOH / tetrahydrofuran / -78 - 20 °C
5: 91 percent / DIPEA / CH2Cl2 / 17 h / 0 - 20 °C
6: 100 percent / p-TsOH*H2O / benzene / 15 h / Heating
7: Na; naphthalene / 1,2-dimethoxy-ethane / 0.25 h / -78 °C
8: 87 percent / PhIO / CH2Cl2 / 3.5 h / 20 °C
9: 84 percent / Yb(OTf)3 / acetonitrile / 0 - 20 °C
10: 85 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
11: 87 percent / NaH / tetrahydrofuran / 20 °C
12: 78 percent / aq. HCl / 26 h / Heating
13: 58 percent / SeO2; MsOH / CH2Cl2 / 0 - 20 °C
14: 84 percent / NaI; BF3*Et2O / acetonitrile / 1.5 h / 0 °C
15: 67 percent / DCC / tetrahydrofuran / 0 - 20 °C
16: 84 percent / K2CO3; 18-crown-6 / toluene / 0 - 20 °C
With
hydrogenchloride; methanol; selenium(IV) oxide; jones reagent; samarium diiodide; naphthalene; methanesulfonic acid; 18-crown-6 ether; iodosylbenzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium; L-Selectride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; sodium iodide; ytterbium(III) triflate;
palladium on activated charcoal;
In
tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; acetone; toluene; acetonitrile; benzene;
1: Catalytic hydrogenation / 2: desilylation / 3: Oxidation / 4: Cyclization / 5: Condensation / 6: cyclocondensation / 7: Reduction / 8: Oxidation / 9: Cycloaddition / 10: Reduction / 11: Etherification / 12: Hydrolysis / 13: Substitution / 14: Substitution / 15: Esterification / 16: Wadsworth-Horner-Emmons cyclization;
DOI:10.1021/jo000260z