Multi-step reaction with 11 steps
1.1: 95 percent / NaH / tetrahydrofuran; various solvent(s) / 3 h / 20 °C
2.1: ozone / CH2Cl2; methanol / -78 °C
2.2: 96 percent / NaBH4 / CH2Cl2; methanol / 4 h / 20 °C
3.1: 68 percent / PPTS / acetone; H2O / 12 h / Heating
4.1: 3.12 g / imidazole / dimethylformamide / 15 h / 20 °C
5.1: 98 percent / KHMDS / tetrahydrofuran / 4 h / -78 - 20 °C
6.1: DPEphos; triethylamine; pinacolborane / Pd(OAc)2 / CH2Cl2 / 1 h / 85 °C
6.2: Cs2CO3 / Pd(PPh3)4 / dimethylsulfoxide / 2 h / 81 °C
6.3: 946 mg / TBAF / tetrahydrofuran / 3 h / 20 °C
7.1: 90 percent / 0.33 h / 165 °C
8.1: 57 percent / triphenylphosphine; diethyl azodicarboxylate / toluene; tetrahydrofuran / 12 h / 20 °C
9.1: 97 percent / m-CPBA / CH2Cl2 / 17 h / 20 °C
10.1: 393 mg / tetrafluoroboric acid / CHCl3 / 22 h / 20 °C
11.1: 253 mg / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C
With
1H-imidazole; tetrafluoroboric acid; pinacol borane; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; bis[2-(diphenylphosphino)phenyl] ether; diethylazodicarboxylate;
palladium diacetate;
In
tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; toluene;
6.2: Suzuki-Miyaura reaction / 8.1: Mitsunobu reaction;
DOI:10.1021/ol060455e