Multi-step reaction with 11 steps
1.1: 99 percent / n-BuLi / tetrahydrofuran; hexane / 0.58 h
2.1: AD mix α; sodium hydrogen carbonate / 2-methyl-propan-2-ol; H2O / 22.5 h / 0 - 5 °C
3.1: 42 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / -78 °C
4.1: 99 percent / lithium borohydride / methanol; tetrahydrofuran / 4 h / 0 °C
5.1: 66 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2
6.1: sodium hydride / dimethylformamide / -50 - -10 °C
7.1: 340 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h
8.1: 95 percent / 4-(dimethylamino)pyridine; Et3N / CH2Cl2 / 0.75 h / 0 °C
9.1: 99 percent / lithium borohydride; ammonium chloride / H2O; tetrahydrofuran / 2.5 h / 0 - 20 °C
10.1: 87 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; molecular sieves / CH2Cl2 / 0.5 h / 20 °C
11.1: lithium diisopropylamide / tetrahydrofuran / 0.42 h / -78 °C
11.2: tetrahydrofuran / 0.42 h
With
2,6-dimethylpyridine; dmap; AD-mix-α; lithium borohydride; n-butyllithium; molecular sieve; tetrapropylammonium perruthennate; ammonium chloride; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
11.2: Julia addition;
DOI:10.1021/ol026034o