Multi-step reaction with 12 steps
1.1: 93 percent / pyridine / 12 h / 0 °C
2.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C
3.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C
4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C
4.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C
5.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C
6.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C
7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating
8.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C
9.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C
9.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C
10.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C
11.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h
12.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating
With
pyridine; 1H-imidazole; quinoline; N,N,N,N,N,N-hexamethylphosphoric triamide; dipyridinium dichromate; tetrabutyl ammonium fluoride; hydrogen; potassium; pyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; tert-butyl alcohol; lithium diisopropyl amide;
bis-triphenylphosphine-palladium(II) chloride; Lindlar's catalyst;
In
tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
1.1: Tosylation / 2.1: Substitution / 3.1: silylation / 4.1: Metallation / 4.2: Addition / 5.1: decyanation / 6.1: Etherification / 7.1: desilylation / 8.1: Oxidation / 9.1: Metallation / 9.2: triflation / 10.1: Condensation / 11.1: Hydrogenation / 12.1: Isomerization;
DOI:10.1016/S0040-4020(97)00139-7
![[(2Z)-2-[(3S,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylenecyclohexylidene]ethyl]diphenylphosphine oxide](/Databaselist/images/loading.webp)
