Multi-step reaction with 28 steps
1: Et3N / 1,2-dimethoxy-ethane / 23 °C
2: (S)-phenylalanine, (+)-camphorsulfonic acid / dimethylformamide / 576 h / 23 °C
3: 1.) potassium hexamethyldisilazide, Et3B / 1.) THF, -78 deg C, 2.) -25 deg C, 2 h
4: HgCl2, water, pyridine / tetrahydrofuran / 36 h / 23 °C
5: Cs2CO3 / tetrahydrofuran / 16 h / 23 °C
6: 77 percent / lithium trisiamylborohydride / tetrahydrofuran / -40 °C
7: 1.) n-BuLi / 1.) ether, -20 deg C, 2.) 23 deg C, 12 h
8: 94 percent / C6H5NMe2 / 1 h / 20 °C
9: 1.) Li, liquid NH3, water / 1.) THF, -40 deg C, 3 min, 2.) -70 deg C, 1 h
10: 0.02percent aq. HCl / acetone / 20 h / 23 °C
11: 1percent aq. KOH / methanol / 6 h / Heating
12: 100 percent / sodium borohydride / tetrahydrofuran; methanol / 1 h / 0 °C
14: 97 percent / methylmagnesium isopropylcyclohexylamide / diethyl ether; toluene / 12 h / 4 °C
15: periodinane / CH2Cl2 / 1 h / 23 °C
16: 1.) Li, liquid NH3, water / 1.) THF, -40 deg C, 3 min, 2.) 30 min
17: 95 percent / NaBH4 / tetrahydrofuran; methanol / 0 °C
18: 98 percent / imidazole / dimethylformamide / 12 h / 50 °C
19: 94 percent / diphenylbromoborane / CH2Cl2 / 0.17 h / -40 °C
20: 95 percent / pyridinium chlorochromate on Al2O3 / CH2Cl2 / 5 h / 23 °C
22: 92 percent / Li, liquid NH3, water / tetrahydrofuran / 0.67 h / -50 °C
23: 1.) n-BuLi / 1.) THF, -20 deg C, 2.) 23 deg C, 2 h
24: Li, EtNH2 / 2-methyl-propan-2-ol / 0.5 h / 0 °C
25: 95 percent / 1percent CF3CO2H / tetrahydrofuran; H2O / 3 h / 23 °C
26: 93 percent / pyridinium chlorochromate on Al2O3 / CH2Cl2 / 5 h / 20 °C
27: 30 percent / diethyl ether / 0.5 h / 0 °C
28: 100 percent / Bu4NF / tetrahydrofuran / 10 h / 50 °C
With
pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; triethyl borane; L-phenylalanine; pyridiniumchlorochromate on aluminumoxide; bromodiphenylborane; tetrabutyl ammonium fluoride; ammonia; water; lithium; potassium hexamethylsilazane; methylmagnesium N-cyclohexylisopropylamide; caesium carbonate; Dess-Martin periodane; ethylamine; N,N-dimethyl-aniline; (+)-10-camphorsulfonic acid; lithium tri-sec-butyl(hydrido)borate; triethylamine; trifluoroacetic acid; mercury dichloride;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;