Multi-step reaction with 23 steps
1.1: [Ir(COD)(Ph2MeP)2]PF6; hydrogen / tetrahydrofuran / 0.58 h / 20 °C
1.2: 9.69 g / iodine / tetrahydrofuran; H2O / 0.08 h / 20 °C
2.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
2.2: 71 percent / tetrahydrofuran / 0 - 20 °C
3.1: 98 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2.5 h / 20 °C
4.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C
4.2: 9.90 g / hydrogen peroxide; sodium hydroxide / tetrahydrofuran / 1.5 h / 20 °C
5.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 0.5 h / 0 °C
6.1: acetic acid / tetrahydrofuran; H2O / 20 °C
7.1: 6.98 g / pyridinium dichromate; molecular sieves 4A / CH2Cl2 / 2 h / 20 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C
8.2: 92 percent / tetrahydrofuran; hexane / -78 - 0 °C
9.1: 79 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C
10.1: N,N'-bis(2,4,6-Me3C6H2CH2)-(S,S)-1,2-Ph2-1,2-diaminoethane; osmium tetroxide / CH2Cl2 / 2 h / -90 °C
10.2: 85 percent / NaHSO3 / tetrahydrofuran; H2O / 2 h / Heating
11.1: 86 percent / camphorsulfonic acid / benzene / 36 h / 20 °C
12.1: 83 percent / sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 0 - 50 °C
13.1: 77 percent / dimethyl sulfide; BF3*Et2O / CH2Cl2 / 0.33 h / 0 °C
14.1: 93 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 0 °C
15.1: 89 percent / dimethylsulfoxide / 5.5 h / 70 °C
16.1: DIBALH / CH2Cl2; toluene / 1 h / -78 °C
16.2: 80 percent / benzene / 1 h / 80 °C
17.1: 97 percent / 2,6-lutidine / CH2Cl2 / 0.67 h / 0 °C
18.1: 89 percent / DIBALH / CH2Cl2; hexane / 0.5 h / -78 °C
19.1: 75 percent / D-(-)-diethyl tartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / molecular sieves 4A / CH2Cl2; 2,2,4-trimethyl-pentane / 5 h / -20 °C
20.1: triethylamine; SO3*pyridine / CH2Cl2; dimethylsulfoxide / 0.5 h / 0 °C
21.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 °C
21.2: 1.081 g / tetrahydrofuran / 0.5 h / 0 °C
22.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C
23.1: 38.9 mg
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; osmium(VIII) oxide; dipyridinium dichromate; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; pyridine-SO3 complex; dimethylsulfide; diethyl (2S,3S)-tartrate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; acetic acid; (1S,2S)-1,2-diphenyl-N1,N2-bis(mesitylmethyl)ethane-1,2-diamine; triethylamine; 9-bora-bicyclo[3.3.1]nonane; lithium hexamethyldisilazane;
4 A molecular sieve;
In
tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
1.1: Hydrolysis / 1.2: Hydrolysis / 2.1: Dehydrobromination / 2.2: methylenation; Wittig reaction / 3.1: Addition / 4.1: hydroboration / 4.2: Oxidation / 5.1: Oxidation / 6.1: Hydrolysis / 7.1: Oxidation / 8.1: Metallation / 8.2: Methylation / 9.1: Addition / 10.1: Oxidation / 10.2: Ring cleavage / 11.1: Cyclization / 12.1: Etherification / 13.1: Hydrolysis / 14.1: Tosylation / 15.1: Substitution / 16.1: Reduction / 16.2: Substitution / 17.1: Etherification / 18.1: Reduction / 19.1: Epoxidation;
DOI:10.1021/jo990988j