Multi-step reaction with 13 steps
1.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 5 h / 0 °C / Inert atmosphere
2.1: dichloromethane / 12 h / 20 °C / Inert atmosphere
3.1: methyllithium / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C / Inert atmosphere
3.2: 0.25 h / -78 - 0 °C / Inert atmosphere
4.1: tetrakis(triphenylphosphine) palladium(0); sodium hydride / tetrahydrofuran; mineral oil / Inert atmosphere
5.1: acetic acid / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere
6.1: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere
7.1: chromium dichloride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere; Glovebox
8.1: dichloro bis(acetonitrile) palladium(II) / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere
9.1: water; m-xylene / 3 h / 160 °C / Inert atmosphere
10.1: diisobutylaluminium hydride / toluene / 0.67 h / -78 - 0 °C / Inert atmosphere
11.1: 1H-imidazole / dichloromethane / 0.42 h / 20 °C / Inert atmosphere
12.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran; acetic acid / 10 h / 20 °C / Inert atmosphere
With
1H-imidazole; chromium dichloride; dichloro bis(acetonitrile) palladium(II); osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; methyllithium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; m-xylene; acetone; toluene; mineral oil;
2.1: |Wittig Olefination / 8.1: |Stille Cross Coupling;
DOI:10.1021/jo401799f