Multi-step reaction with 45 steps
1.1: 9.10 g / CSA / methanol; CHCl3 / 20 °C
2.1: 2,6-lutidine / CH2Cl2 / 0.5 h / -78 °C
2.2: CH2Cl2 / 0.75 h / -78 - 20 °C
3.1: 272.1 mg / CuBr / diethyl ether / 1 h / 0 °C
4.1: OsO4; aq. 4-methylmorpholine N-oxide / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C
4.2: NaIO4 / tetrahydrofuran; 2-methyl-propan-2-ol / 3 h / 20 °C
5.1: BF3*OEt2 / CH2Cl2 / 0.67 h / -78 - 0 °C
6.1: 1.39 g / TBAF / tetrahydrofuran / 20 °C
7.1: 1.57 g / 4-methylmorpholine / CH2Cl2 / 36 h / 20 °C
8.1: 1.27 g / NaHCO3; MeI / acetonitrile; H2O / 35 °C
9.1: SmI2; MeOH / tetrahydrofuran / 0.5 h / 20 °C
9.2: 84 percent / p-TsOH*H2O / toluene / 1 h / 80 °C
10.1: DIBALH / CH2Cl2; hexane / 0.5 h / -78 °C
11.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
11.2: 167.6 mg / tetrahydrofuran / 0.5 h / 0 - 20 °C
12.1: 97 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 0.83 h / 20 °C
13.1: 89 percent / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C
14.1: 100 percent / Et3N / CH2Cl2 / 4 h / 20 °C
15.1: 9-BBN / tetrahydrofuran / 20 °C
15.2: aq. H2O2; NaHCO3 / tetrahydrofuran / 3 h / 20 °C
16.1: H2 / Pd(OH)2/C / methanol / 2.25 h / 20 °C
17.1: 375.3 mg / PPTS / CH2Cl2 / 1 h / 20 °C
18.1: t-BuOK / tetrahydrofuran / 0.33 h / 20 °C
18.2: n-Bu4NI / tetrahydrofuran / 0.83 h / 20 °C
19.1: 356.6 g / DIBALH / CH2Cl2; hexane / 1 h / -78 - 0 °C
20.1: I2; Ph3P; imidazole / benzene / 1 h / 20 °C
21.1: 890.2 mg / t-BuOK / tetrahydrofuran / 0.67 h / 0 °C
22.1: 9-BBN / tetrahydrofuran / 2.5 h / 20 °C
22.2: aq. Cs2CO3 / tetrahydrofuran / 0.33 h / 20 °C
22.3: Pd(PPh3)4 / tetrahydrofuran; dimethylformamide / 50 °C
23.1: BH3*SMe2 / tetrahydrofuran / 1 h / 0 °C
23.2: 1.35 g / aq. H2O2; NaHCO3 / tetrahydrofuran / 2.5 h / 20 °C
24.1: 98 percent / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 1.17 h / 0 °C
25.1: Et3N; LiHMDS / tetrahydrofuran / 0.58 h / -78 °C
26.1: 1.90 g / aq. 4-methylmorpholine N-oxide; OsO4 / 2-methyl-propan-2-ol; tetrahydrofuran / 9 h / 20 °C
27.1: 76 percent / DIBALH / tetrahydrofuran; hexane / 1 h / -78 °C
28.1: Et3N / CH2Cl2 / 0.25 h / 0 °C
29.1: DDQ; phosphate buffer / CH2Cl2 / 1 h / 20 °C / pH 7
30.1: 246.0 mg / tetra-n-propylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH2Cl2 / 2 h / 20 °C
31.1: 79 percent / Zn(OTf)2 / tetrahydrofuran / 72 h / 20 °C
32.1: 97 percent / Et3N / CH2Cl2 / 0.58 h / 0 °C
33.1: m-chloroperbenzoic acid / CH2Cl2 / 2 h / -78 °C
33.2: 92 percent / CH2Cl2; hexane / -78 - 20 °C
34.1: 99 percent / LiDBB / tetrahydrofuran / 0.75 h / -78 °C
35.1: 98 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C
36.1: 78 percent / TBAF; AcOH / tetrahydrofuran / 13 h / 20 °C
37.1: Dess-Martin periodinane / CH2Cl2 / 0.75 h / 20 °C
38.1: K2CO3 / methanol / 17 h / 20 °C
39.1: n-BuLi / tetrahydrofuran; hexamethylphos
With
4-methyl-morpholine; 1H-imidazole; 2,6-dimethylpyridine; methanol; N-iodo-succinimide; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; phosphate buffer; samarium diiodide; tetrapropylammonium perruthennate; copper(I) thiophene-2-carboxylate; tris(dibenzylideneacetone)dipalladium (0); lithium 4,4′-di(tert-butyl)biphenyl; triphenyl-arsane; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; copper(I) bromide; lithium hexamethyldisilazane; methyl iodide;
palladium dihydroxide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
7.1: Michael reaction / 11.2: Wittig reaction / 22.2: Suzuki- Miyaura coupling / 44.1: Stille coupling;
DOI:10.1021/ja066772y