Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 36 h / -15 °C / Molecular sieve
2.1: ozone / dichloromethane / 0.08 h / -78 °C
2.2: 18 h / 20 °C
3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C
4.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C
5.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C
6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 4 h / 20 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C
7.2: 24 h / 20 °C
8.1: potassium tert-butylate / tetrahydrofuran / 6 h / 4 °C
9.1: tetrahydrofuran / 0.5 h / 0 °C
10.1: lithium aluminium tetrahydride; lithium iodide / diethyl ether / -100 - -40 °C
11.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
With
2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; lithium iodide;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethylene dibromide; toluene; acetonitrile;
1.1: Keck allylation / 2.2: Wittig-Horner reaction / 7.1: Wittig-Horner reaction / 7.2: Wittig-Horner reaction / 8.1: Michael condensation;
DOI:10.1002/ejoc.201100888