Multi-step reaction with 11 steps
1.1: N-iodo-succinimide; tetra-(n-butyl)ammonium iodide / dichloromethane / 21 h / 20 °C / Inert atmosphere
2.1: dmap / acetonitrile / 0.67 h / 0 °C / Inert atmosphere
3.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 0.5 h / Inert atmosphere; Reflux
4.1: trimethylaluminum / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere
4.2: 1.5 h / 0 - 20 °C / Inert atmosphere
5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 1.25 h / 0 °C / Inert atmosphere
6.2: 2 h / 0 °C / Inert atmosphere
7.1: iodine / water; tetrahydrofuran / 11 h / 0 °C / Inert atmosphere
8.1: tri-n-butyl-tin hydride / toluene / 0.33 h / Inert atmosphere; Reflux
9.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 19 h / 0 °C / Inert atmosphere
10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere
10.2: 0.5 h / -78 - 20 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere
11.2: 3 h / -78 - 20 °C / Inert atmosphere
With
dmap; N-iodo-succinimide; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; trimethylaluminum; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide;
In
tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile;
3.1: |Barton-McCombie Deoxygenation / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation / 11.1: |Wittig Olefination / 11.2: |Wittig Olefination;
DOI:10.1021/ol501446w