Multi-step reaction with 14 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C
2.2: 0 - 20 °C
3.1: methanol; camphor-10-sulfonic acid / dichloromethane / 12 h / 20 °C
4.1: 1H-imidazole / N,N-dimethyl-formamide / 14.5 h / 50 °C
5.1: methanol; camphor-10-sulfonic acid / dichloromethane / 2 h / 0 °C
6.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 0.5 h / 0 °C
7.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1.5 h / 20 °C
8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C
9.1: tetrakis(triphenylphosphine) palladium(0); hexamethyldistannane; lithium chloride / tetrahydrofuran / 1.5 h / 70 °C
9.2: 3.5 h / 20 °C
10.1: zinc borohydride / diethyl ether / 24 h / -40 °C
11.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C
12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0 - 20 °C / pH 7 / aq. buffer
13.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 6 h / 0 °C
14.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium(0); 2-methyl-but-2-ene; zinc borohydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hexamethyldistannane; sulfur trioxide pyridine complex; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; mineral oil; tert-butyl alcohol;
DOI:10.1021/ol1031409