Multi-step reaction with 11 steps
1.1: 75 percent / BH3 / tetrahydrofuran / 5.5 h / -5 °C
2.1: 65 percent / NaOCl; TEMPO; NaBr / NaHCO3 / toluene; H2O / 3 h / 0 °C
3.1: toluene / 4.5 h / 100 °C
4.1: 87 percent / 9-BBN / tetrahydrofuran / 2 h / 0 °C
5.1: 72 percent / CBr4; PPh3 / CH2Cl2 / 0.5 h / 0 °C
6.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C
6.2: 89 percent / tetrahydrofuran; hexane / 8 h / -78 °C
7.1: aq. HCl / tetrahydrofuran / 12.5 h
8.1: 808 mg / Et3N / tetrahydrofuran / 2.5 h / 20 °C
9.1: 100 percent / aq. LiOH / methanol / 19 h / 0 - 20 °C
10.1: 96 percent / PyBOP; DIEA / CH2Cl2 / 35 h / 0 °C
11.1: 86 percent / H2 / RhCl(PPh3)3 / benzene; ethanol / 96 h / 20686.5 Torr
With
hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; carbon tetrabromide; borane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bromide;
RhCl(PPh3)3; sodium hydrogencarbonate;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; toluene; benzene;
1.1: Reduction / 2.1: Oxidation / 3.1: Wittig reaction / 4.1: Reduction / 5.1: Substitution / 6.1: Metallation / 6.2: Substitution / 7.1: Hydrolysis / 8.1: Acylation / 9.1: Hydrolysis / 10.1: Acylation / 11.1: Catalytic hydrogenation;
DOI:10.1021/ol0065423