Multi-step reaction with 15 steps
1.1: potassium permanganate; water / ethanol / -20 - 20 °C / Inert atmosphere
2.1: dmap; 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3.1: pyridine; lead(IV) acetate / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
3.2: 2 h / 0 - 20 °C / Inert atmosphere
3.3: 1 h / 0 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
5.1: water; 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; iso-butanol / 24 h / 60 °C / Inert atmosphere
6.1: sodium periodate / tetrahydrofuran; water / 1 h / 0 °C / Inert atmosphere
7.1: toluene-4-sulfonic acid; morpholine / toluene / 1 h / 80 °C / Inert atmosphere
8.1: potassium permanganate; aluminum oxide / acetone / 2 h / Inert atmosphere
9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
10.1: dmap / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
11.1: magnesium; iodine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
11.2: 0 - 20 °C / Inert atmosphere
12.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere; Molecular sieve
13.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere
14.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
14.2: 3 h / -78 °C / Inert atmosphere
15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
With
morpholine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; aluminum oxide; potassium permanganate; sodium periodate; osmium(VIII) oxide; n-butyllithium; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; water; iodine; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; iso-butanol;
14.1: |Wittig-Horner Reaction / 14.2: |Wittig-Horner Reaction;
DOI:10.1016/j.bioorg.2022.105660