Multi-step reaction with 13 steps
1.1: 77 percent / NaH / tetrahydrofuran / Heating
2.1: 74 percent / mCPBA / CH2Cl2
3.1: 73 percent / methanol / 50 °C
4.1: hydrogen / 20percent Pd(OH)2 on carbon / dioxane; acetic acid; H2O / 96 h / 2250.23 Torr
4.2: 93 percent / aq. NaOH / dioxane; H2O / pH 8
5.1: 55 percent / triphenylphosphane; di-tert-butyl azodicarboxylate; HN3 / tetrahydrofuran; benzene / 0 - 20 °C
6.1: 69 percent / triphenylphosphane; diisopropyl azodicarboxylate / tetrahydrofuran / -10 - 20 °C
7.1: sulfuryl chloride; acetic anhydride / CH2Cl2 / 1 h / -20 - -5 °C
8.1: 770 mg / triethylamine / CH2Cl2
9.1: 87 percent / NaIO4 / RuCl3*H2O / CH2Cl2; acetonitrile; H2O / 0.33 h / 0 - 20 °C
10.1: 100 percent / hydrogen / Pd/C / ethanol; CHCl3 / 2.5 h / 2250.23 Torr
11.1: 65 percent / triethylamine / tetrahydrofuran
12.1: TFA / CH2Cl2 / 0.5 h
13.1: 133 mg / BOP; DIPEA / CH2Cl2
With
sodium periodate; sulfuryl dichloride; tris-(2-chloro-ethyl)-amine; di-tert-butyl-diazodicarboxylate; di-isopropyl azodicarboxylate; hydrogen; acetic anhydride; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trifluoroacetic acid;
ruthenium trichloride; palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; chloroform; water; acetic acid; acetonitrile; benzene;
1.1: Condensation / 2.1: Epoxidation / 3.1: Addition / 4.1: Hydrogenolysis / 4.2: Condensation / 5.1: Substitution / 6.1: Mitsunobu reaction / 7.1: Substitution / 8.1: Substitution / 9.1: Oxidation / 10.1: Catalytic hydrogenation / 11.1: Substitution / 12.1: Hydrolysis / 13.1: Condensation;
DOI:10.1002/1099-0690(200004)2000:7<1219::AID-EJOC1219>3.0.CO;2-P