Multi-step reaction with 14 steps
1.1: 88 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C
2.1: 99 percent / LiBH4; MeOH / tetrahydrofuran / 4 h / 0 °C
3.1: 82 percent / DMAP; Et3N / CH2Cl2 / 2.75 h / -78 - 20 °C
4.1: NaH / dimethylformamide / 2.5 h / -50 - 20 °C
4.2: 24 percent / TBAF / tetrahydrofuran / 1 h
5.1: 99 percent / Et3N; DMAP / CH2Cl2 / 0.75 h / 0 °C
6.1: 89 percent / LiBH4; aq. NH4Cl / tetrahydrofuran / 3 h / 20 °C
7.1: 95 percent / TPAP; NMO; 4-Angstroem molecular sieves / CH2Cl2 / 0.5 h / 20 °C
8.1: LDA / tetrahydrofuran / 0.42 h / -78 °C
8.2: tetrahydrofuran / 0.42 h
9.1: 114 mg / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 4 h
10.1: Na2HPO4 / tetrahydrofuran; methanol / 0.08 h
10.2: Na/Hg / methanol; tetrahydrofuran / 1 h
11.1: 20.4 mg / PPTS / tetrahydrofuran; H2O / 15 h
12.1: LiDBB / tetrahydrofuran / 0.08 h / -78 °C
13.1: 2.8 mg / TPAP; 4 Angstroem molecular sieves; NMO / 2-methyl-propan-2-ol; acetonitrile
14.1: 78 percent / DIBAL-H / CH2Cl2 / 0.33 h / -78 °C
With
1H-imidazole; methanol; dmap; disodium hydrogenphosphate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; lithium 4,4′-di(tert-butyl)biphenyl; 4 A molecular sieve; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ammonium chloride; triethylamine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
8.2: Julia coupling;
DOI:10.1039/b410092a