Multi-step reaction with 14 steps
1.1: 81 percent / KOH
2.1: n-BuLi / tetrahydrofuran / -78 - 20 °C
2.2: BF3*Et2O / tetrahydrofuran / 0.33 h / -78 °C
2.3: 75 percent / tetrahydrofuran / 1 h / -78 °C
3.1: 77 percent / m-chloroperbenzoic acid / CH2Cl2 / 20 °C
4.1: NaH / dimethylformamide / 0.17 h
4.2: 73 percent / Bu4NI / dimethylformamide / 25 h / 20 °C
5.1: n-BuLi / tetrahydrofuran / 0.17 h / -50 °C
5.2: 434 mg / tetrahydrofuran / 0.5 h / -40 °C
6.1: 32 percent / (S,S)-salen Co(III)OAc; H2O / tetrahydrofuran / 1 h
7.1: n-BuLi / tetrahydrofuran; hexane / 2.5 h / -78 - -40 °C
7.2: Bf3*Et2O / tetrahydrofuran; hexane / 0.17 h / -78 °C
7.3: 59 percent / tetrahydrofuran; hexane / 3 h / -78 °C
8.1: 100 °C
9.1: Pt(DVDS) / tetrahydrofuran; xylene / 20 °C
10.1: aq. H2O2; KF; KHCO3 / tetrahydrofuran; methanol / 20 °C
11.1: Et2BOMe / tetrahydrofuran; methanol / -78 °C
11.2: NaBH4 / tetrahydrofuran; methanol / -78 °C
12.1: K2CO3; MeOH
13.1: TsOH*H2O; 3 Angstroem molecular sieves / 20 °C
14.1: Cp2Zr(H)Cl / tetrahydrofuran / 1.5 h / 20 °C
14.2: 90 percent / I2 / tetrahydrofuran / 0.25 h
With
methanol; potassium fluoride; potassium hydroxide; Schwartz's reagent; n-butyllithium; bis(η2:η2-1,3-divinyltetramethyl)platinum(0); (S,S)-salen Co(III)OAc; 3 A molecular sieve; diethyl methoxy borane; water; dihydrogen peroxide; sodium hydride; potassium carbonate; potassium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; xylene;
DOI:10.1021/ja039618+