Multi-step reaction with 14 steps
1.1: 93 percent / PPh3; imidazole; I2 / tetrahydrofuran / 2 h / 0 °C
2.1: 99 percent / hypophosphorous acid; 1-ethylpiperidine; Et3B / ethanol / 0.5 h / 20 °C
3.1: 100 percent / KOH / H2O; methanol; tetrahydrofuran / 3 h / 20 °C
4.1: 97 percent / BH3*DMS; B(OMe)3 / tetrahydrofuran / 3 h / 20 °C
5.1: 91 percent / sulfur trioxide; pyridine / dimethylsulfoxide; CH2Cl2 / 1 h / 0 °C
6.1: (+)-DIP-chloride / tetrahydrofuran / 2 h / -78 - 20 °C
6.2: 92 percent / NaOH; H2O2 / tetrahydrofuran / 0.17 h / 20 °C
7.1: 100 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 12 h / 20 °C
8.1: 97 percent / Ti(O-iPr)4 / 1,2-dimethoxy-ethane / 48 h / Heating
9.1: OsO4; 4-methylmorpholine N-oxide / H2O; acetone / 20 °C
9.2: 89 percent / NaIO4 / H2O; acetone / 0.5 h / 20 °C
10.1: KO-t-Bu; n-BuLi; B(dIpc)2OMe / tetrahydrofuran / -78 - -45 °C
10.2: 82 percent / NaOH; H2O2 / tetrahydrofuran; H2O / 1 h / 20 °C
11.1: 100 percent / 2,6-lutidine / CH2Cl2 / 3 h / 0 °C
12.1: 4-methylmorpholine N-oxide; OsO4 / acetone; H2O / 24 h / 20 °C
12.2: 93 percent / NaIO4 / acetone; H2O / 0.5 h
13.1: 99 percent / NaBH4 / ethanol / 0.5 h / 20 °C
14.1: 100 percent / Ph3P; DIAD / tetrahydrofuran / 1 h / 0 °C
With
1-ethyl-piperidine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Trimethyl borate; triethyl borane; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; B(dIpc)2OMe; sulfur trioxide; potassium tert-butylate; iodine; hypophosphorous acid; sodium hexamethyldisilazane; 4-methylmorpholine N-oxide; triphenylphosphine; B-chlorodiisopinocampheylborane;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
6.1: Brown allylation / 10.1: Brown crotylation;
DOI:10.1021/jo0507993