Multi-step reaction with 8 steps
1.1: copper(II) sulfate; sulfuric acid / 1 h / 23 °C
2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 23 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C
4.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide; dichloromethane / 0.17 h / -20 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C
5.2: 3 h / -78 °C
6.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 23 °C
8.1: pyridinium chlorochromate; sodium acetate / dichloromethane / 6 h / 0 - 23 °C / Molecular sieve
With
sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium acetate; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; sodium hydride; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil;
4.1: |Parikh-Doering Oxidation / 5.1: |Sakurai Allylation / 5.2: |Sakurai Allylation;
DOI:10.1021/jo401166q