Multi-step reaction with 12 steps
1: 88 percent / NaH; i-Pr2NEt / tetrahydrofuran / 3 h / 0 - 18 °C
2: 60 percent / DIBAL-H / toluene / 7.5 h / -30 °C
3: 66 percent / triiodoimidazole; imidazole; PPh3 / toluene / 5 h / Heating
4: 84 percent / n-Bu3SnH; Et3B; O2 / toluene; hexane / 2 h / 18 °C
5: 98 percent / DDQ / CH2Cl2; H2O / 20 h / 18 °C
6: 75 percent / diphenylphosphoryl azide; DEAD; PPh3 / CH2Cl2 / 18 h / 18 °C
7: 98 percent / PPh3; H2O / tetrahydrofuran / 20 h / 65 °C
8: benzene / 16 h / Heating
9: sodium cyanoborohydride / methanol / 1 h / 18 °C
10: 74 percent / EDCI; HOBt; i-Pr2NEt / dimethylformamide / 3 h / 30 °C
11: n-Bu3SnH; n-Bu6Sn2; AIBN / benzene / 3 h / 80 °C / Irradiation
12: 94 percent / LiAlH4; AlCl3 / tetrahydrofuran / 12 h / 18 °C
With
1H-imidazole; lithium aluminium tetrahydride; aluminium trichloride; 2,2'-azobis(isobutyronitrile); triethyl borane; tri-iodoimidazole; diphenylphosphoranyl azide; water; oxygen; tri-n-butyl-tin hydride; bis(tri-n-butyltin); sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
6: Mitsunobu reaction / 7: Staudinger reaction;
DOI:10.1021/ol071344y