Multi-step reaction with 20 steps
1.1: 1H-imidazole / tetrahydrofuran / 24 h / 0 - 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C
3.1: potassium iodide; sodium hydride / tetrahydrofuran / 6 h / 60 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C
5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
7.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere
8.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -30 °C / Inert atmosphere
8.2: 15 h / -30 °C / Inert atmosphere
9.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere
10.1: dichloromethane / 2 h / 20 °C / Inert atmosphere
11.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7 h / -30 - 20 °C / Inert atmosphere
12.1: ozone / methanol; dichloromethane / 2 h / -70 °C
13.1: sodium tetrahydroborate / methanol; dichloromethane / 23 h
14.1: triethylamine; dmap / dichloromethane / 14 h / 20 °C
15.1: sodium hydride / tetrahydrofuran / 17 h / 0 - 20 °C
16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
17.1: naphthalene; sodium / 1,2-dimethoxyethane / -70 °C / Inert atmosphere
18.1: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 18 h / 20 °C
19.1: palladium on carbon; hydrogen; hydrogenchloride / methanol / 2 h / 0 - 20 °C
20.1: triethylamine; dmap / dichloromethane / 1 h / 20 °C
With
1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; naphthalene; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; palladium on carbon; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; potassium iodide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; acetonitrile;
5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 9.1: |Dess-Martin Oxidation / 10.1: |Wittig Olefination;
DOI:10.1016/j.tet.2013.03.012