Multi-step reaction with 10 steps
1.1: 1,5-hexadiene; SOBr2 / 1,2-dichloro-ethane / 1.5 h / 0 °C
2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C
2.2: 48 percent / tetrahydrofuran / 3.5 h / -78 °C
3.1: NMMO*H2O / OsO4 / tetrahydrofuran; H2O / 1 h / 25 °C
4.1: H2O2; LiOH*H2O / tetrahydrofuran; H2O / 0.75 h / 0 °C
5.1: 2.74 g / TFA / tetrahydrofuran / 3.75 h / 0 °C
6.1: 34 percent / Et3N; DMAP / CH2Cl2 / 2.2 h / 0 °C
7.1: LiOH*H2O / tetrahydrofuran; H2O / 15 h / 25 °C
7.2: 2,6-lutidine / dimethylformamide / 1.5 h / 0 °C
8.1: 0.80 g / aq. NaOH / tetrahydrofuran / 1 h / 0 °C
9.1: 0.76 g / i-Pr2NEt; BOP*PF6 / CH2Cl2 / 1.7 h / 20 °C
10.1: 79 percent / aq. HF / acetonitrile / 1.8 h / 20 °C
With
dmap; lithium hydroxide; sodium hydroxide; sulfurous dibromide; 1,5-Hexadien; NMMO*H2O; hydrogen fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid;
osmium(VIII) oxide;
In
tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile;
1.1: Substitution / 2.1: Metallation / 2.2: Evans' alkylation / 3.1: Oxidation / 4.1: Hydrolysis / 5.1: Cyclization / 6.1: Esterification / 7.1: Hydrolysis / 7.2: silylation / 8.1: Hydrolysis / 9.1: Acylation / 10.1: Hydrolysis;
DOI:10.1016/S0968-0896(98)80011-4