Multi-step reaction with 16 steps
1.1: LiI; HN(TMS)2 / CH2Cl2 / 3 h
2.1: 84 percent / tetrahydrofuran; pyridine / 0.5 h / -78 °C
3.1: 83 percent / MCPBA / CH2Cl2 / 0.5 h
4.1: 80 percent / NaBH4; CeCl3*7H2O / methanol / 1 h
5.1: 90 percent / NaH; tetrabutylammonium iodide / tetrahydrofuran / 3 h / Heating
6.1: BH3*SMe2 / tetrahydrofuran / 3 h / 20 °C
6.2: 62 percent / H2O2; NaOH / ethanol; H2O / 1 h / Heating
7.1: 91 percent / iPr2EtN / CH2Cl2 / 3 h / 20 °C
8.1: 100 percent / H2 / Pd/C / ethanol / 1.5 h
9.1: 97 percent / PDC; 4-Angstroem molecular sieves / CH2Cl2 / 2 h
10.1: 90 percent / LiN(TMS)2 / tetrahydrofuran / 2 h / 20 °C
11.1: 80 percent / LiCl / Pd(PPh3)4 / tetrahydrofuran / 4 h / Heating
12.1: 87 percent / O2; 5,10,15,20-tetraphenyl-21H,23H-porphine / CH2Cl2 / 2 h / -78 °C / Irradiation
13.1: 100 percent / NaNO2; H2 / PtO2 / ethanol / 3 h
14.1: 86 percent / H2; NaNO2 / Pt/C / ethyl acetate / 2 h
15.1: 79 percent / pyridine; DMAP / CH2Cl2 / 1.5 h
16.1: 62 percent / NaH; TBAI / tetrahydrofuran / 2 h / Heating
With
pyridine; dmap; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; dimethylsulfide borane complex; 4 A molecular sieve; hydrogen; oxygen; 5,15,10,20-tetraphenylporphyrin; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; lithium chloride; lithium iodide; lithium hexamethyldisilazane; sodium nitrite;
platinum(IV) oxide; palladium on activated charcoal; platinum on activated charcoal; tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; ethyl acetate;
1.1: Silylation / 2.1: Selenenylation / 3.1: Elimination / 4.1: Reduction / 5.1: Etherification / 6.1: Hydroboration / 6.2: Oxidation / 7.1: Etherification / 8.1: Hydrogenolysis / 9.1: Oxidation / 10.1: Substitution / 11.1: Vinylation; Stille coupling / 12.1: Cycloaddition / 13.1: Adam's reduction / 14.1: Hydrogenation / 15.1: Acylation / 16.1: Benzylation;
DOI:10.1002/(SICI)1099-0690(200002)2000:3<439::AID-EJOC439>3.0.CO;2-F