Multi-step reaction with 13 steps
1.1: dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: triethylamine; sodium hydrogencarbonate; water / dichloromethane / 3 h / 20 °C / pH >7
3.1: triethylamine / dichloromethane / 0 - 20 °C
4.1: sodium iodide / acetone / 24 h / Reflux
4.2: 1 h / Reflux
5.1: pyridinium p-toluenesulfonate / dichloromethane / 10 h / 20 °C
6.1: lithium; naphthalene / tetrahydrofuran / 0.5 h / -10 °C
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere
8.1: tetrahydrofuran / 0 - 20 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 °C / Inert atmosphere
10.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere
11.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere
11.2: 5 h / 20 °C
12.1: ozone / dichloromethane; methanol / -78 °C / Inert atmosphere
12.2: -78 °C
13.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere
With
sodium tetrahydroborate; naphthalene; tributylphosphine; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; water; pyridinium p-toluenesulfonate; lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ozone; triethylamine; sodium iodide;
In
tetrahydrofuran; methanol; dichloromethane; acetone;
1.1: |Prins-Kriewitz Hydroxyinethylation / 13.1: |Mitsunobu Displacement;
DOI:10.1021/jo302205t