Multi-step reaction with 12 steps
1: 85 percent / LiHMDS; HMPA / tetrahydrofuran / 0.08 h / -40 °C
2: 77 percent / NaBH4; DPPP / Pd(OAc)2 / dimethylsulfoxide
3: 44 percent / Grubbs second generation catalyst / benzene / 16 h / 20 °C
4: 93 percent / dimethyl sulfide; MgBr2*Et2O / CH2Cl2 / 0.67 h / 20 °C
5: (S,S)-N-[2-(2-PPh2-benzoylamino)cyclohexyl]-2-PPh2-benzamide / Pd2dba3*CHCl3 / CH2Cl2 / 20 °C
6: 1,2-dimethoxy-ethane / 1 h / 150 °C / microwave irradiation
7: Cs2CO3; Bu4NI / dimethylformamide / 2 h
8: 8.7 mg / pyridine / 3 h / 20 °C
9: 65 percent / AD-α-mix; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 48 h / 4 °C
10: NaIO4 / tetrahydrofuran; H2O / 1 h / 20 °C
11: 6.5 mg / NaBH4 / CH2Cl2; methanol / 0.5 h / -78 °C
12: 89 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / 20 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); lithium hydroxide; sodium tetrahydroborate; sodium periodate; AD-mix-α; dimethylsulfide; methanesulfonamide; 1,3-bis-(diphenylphosphino)propane; tetra-(n-butyl)ammonium iodide; caesium carbonate; magnesium bromide; lithium hexamethyldisilazane;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; palladium diacetate;
In
tetrahydrofuran; pyridine; methanol; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene;
6: Claisen rearrangement / 9: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja070571s