Multi-step reaction with 10 steps
1: 1.) s-BuLi, (+)-DIP-OMe, 2.) BF3*Et2O, 3.) NaOAc, H2O2 / 1.) THF, 15 min, -78 deg C, 30 min, 2.) THF, -78 deg C for 30 min then 0 deg C for 30 min, 3.) 18 h
2: 88 percent / Ph3P, EtOOCN=NCOOEt, (PhO)2P(O)N3 / tetrahydrofuran / 0 deg C, 1 h; 25 deg C, 2 h
3: 90 percent / 2M HCl / dioxane; methanol / 18 h / 25 °C
4: 95 percent / D-diisopropyl tartarate, Ti(OiPr)4, t-BuOOH, 4 Angstroem molecular sieves / CH2Cl2 / 36 h / -15 °C
5: 80 percent / 10percent TBAI, NaH / tetrahydrofuran / 1 h / 25 °C
6: 82 percent / CuCN / tetrahydrofuran / 4 h / 0 °C
7: 89 percent / Ph3P, EtOOCN=NCOOEt, (PhO)2P(O)N3 / tetrahydrofuran / 36 h / -10 °C
8: 85 percent / PPh3 / tetrahydrofuran; H2O / 4 h / 80 °C
9: 75 percent / Na(OAc)3BH / acetic acid; 1,2-dichloro-ethane / 18 h / 25 °C
10: 50 percent / Et3N / CHCl3 / 18 h / -40 -> 25 deg C
With
titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; (+)-DIP-OMe; 4 A molecular sieve; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; dihydrogen peroxide; sec.-butyllithium; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium tris(acetoxy)borohydride; sodium hydride; diisopropyl-d0 D-tartrate; triethylamine; triphenylphosphine; diethylazodicarboxylate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform; water; acetic acid; 1,2-dichloro-ethane;
DOI:10.1016/0040-4039(96)00013-5