Multi-step reaction with 19 steps
1.1: methanol; sodium methylate / 1 h / 20 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
3.1: sodium hydride / tetrahydrofuran; mineral oil / 2 h / 0 - 20 °C / Inert atmosphere
3.2: 0 - 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C / Inert atmosphere
5.2: 0 - 20 °C / Inert atmosphere
6.1: tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 2-phenyl-1,4-benzoquinone / dichloromethane / 0.08 h / 55 °C / Inert atmosphere; Molecular sieve
6.2: 48 h / 55 °C / Inert atmosphere; Molecular sieve
7.1: sodium methylate / methanol / 2 h / 20 °C / Inert atmosphere
7.2: 20 °C / Inert atmosphere
8.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.75 h / -40 °C / Inert atmosphere; Molecular sieve
8.2: 24 h / -40 - -20 °C / Inert atmosphere
9.1: 1H-imidazole; iodine; triphenylphosphine / diethyl ether; benzene / 0.67 h / 20 °C / Inert atmosphere
10.1: zinc / ethanol / 0.75 h / Inert atmosphere; Reflux
11.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / Inert atmosphere; Reflux
12.1: dichloromethane / 0.5 h / 20 °C / Inert atmosphere
13.1: water; potassium carbonate / methanol / 20 °C / Inert atmosphere
14.1: triethylamine; trifluoroacetic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
15.1: tributyltin methoxide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere
16.1: sodium hydroxide / tetrahydrofuran; ethanol; water / 4 h / 20 °C / Inert atmosphere
17.1: water; potassium hydroxide / ethanol / 1 h / Sealed vial; Reflux
18.1: ammonia; sodium / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere
18.2: -78 °C / Inert atmosphere
19.1: triethylamine / tetrahydrofuran; methanol / 2 h / 0 - 20 °C / Inert atmosphere
With
1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; methanol; tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate); L-(+)-diisopropyl tartrate; tetrabutyl ammonium fluoride; ammonia; water; iodine; sodium methylate; tributyltin methoxide; sodium; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2-phenyl-1,4-benzoquinone; trifluoroacetic anhydride; potassium hydroxide; sodium hydroxide; zinc;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; benzene;
8.1: Sharpless epoxidation / 8.2: Sharpless epoxidation / 18.1: Birch reduction;
DOI:10.1021/ol2032448