Multi-step reaction with 10 steps
1.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere
1.2: 2 h / 0 °C / Inert atmosphere
2.1: sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 2 h / pH 7 / Inert atmosphere; aq. buffer
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
3.2: 1 h / 0 °C / Inert atmosphere
4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 18 h / 20 °C / Inert atmosphere
5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 - -40 °C / Inert atmosphere
5.2: 2 h / -78 - 20 °C
6.1: dimethyl zinc(II); tert.-butyl lithium / tetrahydrofuran; n-heptane; pentane / 1.75 h / -78 °C / Inert atmosphere
6.2: 3 h / -78 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 0 - 20 °C
8.1: camphor-10-sulfonic acid / 12 h / 20 °C / Inert atmosphere
9.1: 1H-imidazole / dichloromethane / 12 h / 20 °C / Inert atmosphere
10.1: dmap; N-ethyl-N,N-diisopropylamine; sodium iodide / dichloromethane / 12 h / 0 - 20 °C
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium periodate; osmium(VIII) oxide; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl zinc(II); tert.-butyl lithium; sodium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium iodide;
In
tetrahydrofuran; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil; pentane;
3.1: Wittig reaction / 3.2: Wittig reaction / 5.1: Swern oxidation / 5.2: Swern oxidation;
DOI:10.1021/ol201920j