Multi-step reaction with 15 steps
1.1: 2,6-dimethylpyridine / dichloromethane / 20 °C / Inert atmosphere
2.1: methanol; diethyl ether / 0 °C / Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere
4.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / Inert atmosphere
5.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / Inert atmosphere
6.1: sodium periodate / water; acetone / 20 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere
7.2: Inert atmosphere
8.1: palladium diacetate; triphenylphosphine; tri-n-butyl-tin hydride / tetrahydrofuran / 20 °C / Inert atmosphere
9.1: dimethylsulfide borane complex / tetrahydrofuran / 10 h / 20 °C / Inert atmosphere
9.2: 3 h / Inert atmosphere
10.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere
11.1: hydrogen fluoride / water; acetonitrile / 10 h / 20 °C / Inert atmosphere
12.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
12.2: 2 h / Inert atmosphere
13.1: tetrahydrofuran; mineral oil / 10 h / Inert atmosphere
14.1: o-xylene / Inert atmosphere; Reflux
15.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 5 h / 20 °C / Inert atmosphere
With
2,6-dimethylpyridine; potassium osmate(VI) dihydrate; sodium periodate; lithium aluminium tetrahydride; dipyridinium dichromate; dimethylsulfide borane complex; hydrogen fluoride; tri-n-butyl-tin hydride; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; o-xylene; water; N,N-dimethyl-formamide; acetone; acetonitrile; mineral oil;
12.1: |Chugaev Elimination Reaction;
DOI:10.1002/cjoc.201201039