Multi-step reaction with 10 steps
1: 1.) 9-BBN, 2.) Na2O2 / 1.) THF
2: PCC, Celite, Fluorisil, NaOAC / CH2Cl2
3: tetrahydrofuran / -90 °C
4: 1.) NaH, 2.) n-Bu4NI / 1.) DMF
5: 86 percent / NBS, NaHCO3 / acetonitrile
6: 1.) Swern's oxid. / 2.) CH2Cl2
7: 1.) DDQ, MS 4A, 2.) LAH / 1.) CH2Cl2, 2.) ether
8: 1.) NaBH4, 2.) pyridine / 1.) EtOH, 2.) CH2Cl2
9: 80 percent / I2, Ph3P, imidazole / benzene
10: 92 percent / Zn, NH4Cl / ethanol / Heating
With
pyridine; 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; sodium peroxide; Florisil; Celite; Swern's oxid; iodine; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; ammonium chloride; triphenylphosphine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc;
In
tetrahydrofuran; ethanol; dichloromethane; acetonitrile; benzene;
DOI:10.1021/jo00284a030