Multi-step reaction with 15 steps
1.1: DIABLH / CH2Cl2 / -78 °C
1.2: NaBH4 / methanol / 0 °C
2.1: Et3N; DMAP / CH2Cl2 / 20 °C
3.1: dimethylsulfoxide / 70 °C
3.2: Mg / methanol / 20 °C
3.3: 83 percent / imidazole / dimethylformamide / 20 °C
4.1: DIABLH / CH2Cl2 / -78 °C
4.2: AcOH / tetrahydrofuran; H2O / 20 °C
4.3: 78 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 20 °C
5.1: 82 percent / LiHMDS / tetrahydrofuran / -78 °C
6.1: 68 percent / tetrahydrofuran / -78 °C
7.1: OsO4; N,N'-bis(2,4,6-triMe-Bn)-(S,S)-1,2-diPh-1,2-diaminoethane / CH2Cl2 / -90 °C
7.2: NaHSO3 / tetrahydrofuran; H2O / 70 °C
7.3: 79 percent / camphorsulfonic acid / benzene / 20 °C
8.1: 98 percent / NaH / dimethylformamide / 20 °C
9.1: BF3*Et2O; Me2S / CH2Cl2 / 0 °C
9.2: NaHMDS / tetrahydrofuran / 40 °C
10.1: 2,6-lutidine / CH2Cl2 / 20 °C
11.1: 9-BBN / tetrahydrofuran / 20 - 40 °C
11.2: 98 percent / NaOH; H2O2 / H2O / 20 °C
12.1: SO3*pyridine; Et3N / CH2Cl2; dimethylsulfoxide / 0 °C
12.2: NaClO2; KH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 20 °C
13.1: 0.5 M HCl / tetrahydrofuran / 20 °C
14.1: 2,4,6-trichlorobenzoyl chloride; Et3N / tetrahydrofuran
14.2: 93 percent / DMAP / benzene / Heating
15.1: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C
With
2,6-dimethylpyridine; hydrogenchloride; dmap; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; pyridine-SO3 complex; dimethylsulfide; 2,4,6-trichlorobenzoyl chloride; boron trifluoride diethyl etherate; sodium hydride; (1S,2S)-1,2-diphenyl-N1,N2-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; lithium hexamethyldisilazane;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
6.1: Grignard reaction / 9.2: Wittig reaction;
DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W