Multi-step reaction with 18 steps
1.1: 94 percent / DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C
2.1: Zn-Cu; DMA / benzene / 1 h / Heating
2.2: 85 percent / PdCl2(o-Tol3P)2 / benzene / 13 h / 40 °C
3.1: BH3*SMe2 / tetrahydrofuran / 2 h / 20 °C
3.2: aq. NaOH; H2O2 / tetrahydrofuran / 1 h / 20 °C
4.1: 76 percent / 2,6-lutidine / CH2Cl2 / 2.5 h / 20 °C
5.1: 56 percent / aq. AcOH / tetrahydrofuran / 3 h / 20 °C
6.1: 90 percent / Bu3P / dimethylformamide / 2 h / 0 - 20 °C
7.1: NCS / CCl4; CH2Cl2 / 0.5 h / 20 °C
8.1: 146 mg / DTBMP; AgOTf; 4 Angstroem molecular sieves / CH2Cl2 / 1 h / -10 °C
9.1: TBAF / tetrahydrofuran / 3 h / 20 °C
10.1: CSA / CH2Cl2 / 1 h / 20 °C
10.2: TMSI; HMDS / CH2Cl2 / 1 h / 0 °C
10.3: AgOTf; 4 Angstroem molecular sieves / CH2Cl2 / 3 h / 20 °C
11.1: 72 percent / Grubbs catalyst / benzene / 13 h / 60 °C
12.1: CSA / CH2Cl2; methanol / 2 h / 20 °C
13.1: 2,6-lutidine / CH2Cl2 / 1 h / 20 °C
14.1: H2; Et3N / Pd/C / ethyl acetate / 2 h
15.1: 53.4 mg / CSA / CH2Cl2; methanol / 2.5 h / 0 °C
16.1: NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
17.1: tetrahydrofuran; diethyl ether / 0.5 h / 0 °C
18.1: 43.0 mg / NMO; TPAP; 4 Angstroem molecular sieves / CH2Cl2 / 2 h / 20 °C
With
2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-chloro-succinimide; Grubbs catalyst first generation; N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; tetrapropylammonium perruthennate; tributylphosphine; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; silver trifluoromethanesulfonate; potassium hexamethylsilazane; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; acetic acid; triethylamine; zinc;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja051171c