Multi-step reaction with 12 steps
1: 73.5 percent / acetonitrile / 72 h / Heating
2: 93 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / -78 - 20 °C
3: 60.4 percent / dihydroquinidine acetate, OsO4 / toluene / 5 h
4: 96 percent / H2 / 10percent Pd(OH)2/C / ethyl acetate / 2 h
5: 80 percent / 4A molecular sieves, camphorsulfonic acid / benzene; tetrahydrofuran / 2 h / Ambient temperature
6: 95 percent / dicyclohexylcarbodiimide (DCC) / CH2Cl2 / 0.33 h
7: 90.8 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / -15 - -10 °C
8: N-metylmorpholine, (benzotriazolyl-1-oxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) / CH2Cl2 / 3 h / Ambient temperature
9: 10percent aq. HCl / tetrahydrofuran / 0.08 h
10: Dess-Martin periodinane / CH2Cl2 / 1.5 h
11: LiCl, diazobicycloundecene (DBU) / acetonitrile / 2.5 h
12: 67.5 percent / Et2AlCl, propanedithiol / CH2Cl2 / 4 h / Ambient temperature
With
4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; osmium(VIII) oxide; hydroquinidine acetate; 1,2-propanedithiol; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; diethylaluminium chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium chloride;
palladium dihydroxide;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;