Multi-step reaction with 19 steps
1: HNO2, NaN3
2: PCC
3: NaOH
4: 100 percent / n-Bu4NF / tetrahydrofuran / -78 °C
5: 85 percent / BF3-Et2O / CH2Cl2
6: 81 percent / ethanol
7: 91 percent / Ph3P, AcOH / methanol; tetrahydrofuran / 23 °C
8: 1.) DIBAL, 2.) NaBH3CN, TFA / 1.) CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2
9: pyridine / CH2Cl2
10: pyridine
11: 99 percent / HgCl2 / methanol / Heating
12: MCPBA / CH2Cl2
13: toluene / 175 °C
14: 70 percent / NaOH/H2O / methanol / Heating
15: 89 percent / 2-(phenylsulfonyl)-3-phenyloxaziridine (Davis' reagent) / tetrahydrofuran / 23 °C
16: 85 percent / 23 °C
17: 78 percent / MCPBA, NaHCO3 / CH2Cl2 / 23 °C
18: 1.) (COCl)2, Et3N, 2.) H2NNH2 / 1.) DMSO, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 0 deg C
19: 60 percent / CSA, quinoline / benzene / Heating
With
pyridine; quinoline; sodium hydroxide; sodium azide; oxalyl dichloride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; cis-nitrous acid; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; acetic acid; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; mercury dichloride; hydrazine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4039(01)89002-X