Multi-step reaction with 11 steps
1.1: (-)-B-methoxydiisopinocamphenylborane / diethyl ether / 1 h / 0 - 20 °C
1.2: 3 h / -78 °C
2.1: sodium hydride / tetrahydrofuran / 1 h / -10 - 20 °C
2.2: 12 h / 20 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 0 - 20 °C
3.2: 2 h / Reflux
4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 2 h / -10 °C
5.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / water; tert-butyl alcohol / 1 h / -10 - 20 °C
6.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 0 - 20 °C
7.1: pyridine; dmap / dichloromethane / 20 °C
8.1: tetrahydrofuran / 1 h / -78 °C
8.2: 0.03 h / -78 °C / Molecular sieve
9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 8 h / 20 °C
10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1.5 h / 20 °C
11.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 2 h / 0 °C
With
pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; (-)-B-methoxydiisopinocamphenylborane; sulfur trioxide pyridine complex; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.3987/COM-12-S(N)54