Multi-step reaction with 12 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2.5 h / 0 °C / pH 7 / aq. buffer
2.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene / 4 h / -30 °C
3.1: pyridinium p-toluenesulfonate / dichloromethane / 0 - 20 °C
4.1: copper(I) thiophene-2-carboxylate / 1-methyl-pyrrolidin-2-one / 16 h / 20 °C
5.1: methanol; potassium fluoride / tetrahydrofuran / 2 h / 20 °C
6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 20 °C
6.2: 0.33 h / 20 °C
7.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 0 - 20 °C
8.1: 2,6-dimethylpyridine / dichloromethane / -98 - 20 °C
9.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.17 h / 20 °C
9.2: 1.5 h / 20 °C
10.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2.08 h / 0 - 20 °C
11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C
11.2: -78 - 0 °C
12.1: pyridine hydrogenfluoride / tetrahydrofuran; pyridine / 0 - 20 °C
With
2,6-dimethylpyridine; methanol; potassium fluoride; borane-THF; copper(I) thiophene-2-carboxylate; 2,4,6-trichlorobenzoyl chloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; pyridine; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; toluene;
4.1: Stille-Liebeskind cross coupling / 6.1: Yamaguchi macrolactonization / 6.2: Yamaguchi macrolactonization;
DOI:10.1002/asia.201000541