Multi-step reaction with 16 steps
1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.33 h / 0 °C
2.1: toluene / 43 h / 20 °C
3.1: nickel dichloride; sodium tetrahydroborate / methanol / 0 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 °C
5.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C
6.1: dimethyl sulfoxide / 2.5 h / 60 °C
7.1: potassium hydroxide / water; ethanol / 18 h / 80 °C
8.1: triethylamine / tetrahydrofuran / 3 h / -78 - 0 °C
9.1: lithium chloride / tetrahydrofuran / 33 h / 20 °C
10.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C
10.2: 4 h / -78 °C
11.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 0 - 20 °C / pH 7
12.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0.75 h / 0 °C
13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 0.5 h / 0 - 20 °C
13.2: 1 h / 110 °C
14.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -78 °C
15.1: dmap; pyridine / dichloromethane; hexane / 4 h / -78 °C
16.1: 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C
With
pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; lithium hydroxide monohydrate; trimethylsilyl trifluoromethanesulfonate; 2,4,6-trichlorobenzoyl chloride; dihydrogen peroxide; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; diisobutylaluminium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; potassium hydroxide; nickel dichloride;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
13.1: |Yamaguchi Lactonization / 13.2: |Yamaguchi Lactonization;
DOI:10.1021/jo4025545