Multi-step reaction with 24 steps
1: 64 percent / LDA / tetrahydrofuran / -78 °C
2: 95 percent / C3H4N2 / dimethylformamide / 60 °C
3: 73 percent / tetrahydrofuran / -78 °C
4: 96 percent / C5H5N(1+)*HBr3(1-), C5H5N / 0 °C
5: 1.) DIBAL-H / 1.) toluene, -78 deg C, 2.) THF, 0 deg C
6: C3H4N2 / dimethylformamide / 60 °C
7: 70 percent / 1,3-di(9-phosphafluoren-9-yl)propane, 2-(diphenylphosphino)benzoic acid, palladium acetate / 1,2-dichloro-ethane / 60 °C
8: 89 percent / TBAF / tetrahydrofuran / Ambient temperature
9: 1.) SOCl2, 2.) CsOAc, 3.) K2CO3
10: 1.) (COCl)2, (C2H5)3N, 2.) NaClO2, (CH3)2C=CHCH3, NaH2PO4
11: 63 percent / CF3CO3H, CSA / CH2Cl2 / Heating
12: 75 percent / OsO4, C5H5N / Ambient temperature
13: 96 percent / Zn, HOAc / methanol / 60 °C
14: 70 percent / TsOH / acetone
15: 1.) aq. KOH / 1.) CH3OH, RT, 2.) ether, 0 deg C
16: 86 percent / (C2H5)3N, DMAP / CH2Cl2
17: 67 percent / aq. HCl / tetrahydrofuran / Ambient temperature
18: 85 percent / lutidine / 1,2-dichloro-ethane / Ambient temperature
19: 90 percent / NaCN / methanol; tetrahydrofuran / Ambient temperature
20: 68 percent / t-C4H9OLi, t-C4H9OH / toluene / 100 °C
21: 92 percent / aq. HF / acetonitrile / 100 °C
22: 85 percent / (CF3SO2)2O, N-methylimidazole / 100 °C
23: 71 percent / LiBH4, HOAc / tetrahydrofuran / 0 °C
24: 98 percent / TMS-Cl / acetonitrile / Ambient temperature
With
pyridine; 1-methyl-1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; chloro-trimethyl-silane; thionyl chloride; 2-methyl-but-2-ene; oxalyl dichloride; trifluoromethylsulfonic anhydride; trifluoroacetyl peroxide; 1,3-di(9-phosphafluoren-9-yl)propane; lutidine; camphor-10-sulfonic acid; ortho-diphenylphosphinobenzoic acid; hydrogen fluoride; sodium cyanide; tetrabutyl ammonium fluoride; cesium acetate; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; triethylamine; lithium tert-butoxide; zinc; tert-butyl alcohol; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
DOI:10.1021/ja953060r