Multi-step reaction with 12 steps
1.1: boron trifluoride diethyl etherate / diethyl ether / 0 °C
2.1: sodium periodate; ruthenium trichloride; water; zinc(II) chloride / ethyl acetate; acetonitrile / 0 °C
3.1: toluene-4-sulfonic acid / tetrahydrofuran / 40 °C
4.1: sodium tetrahydroborate / methanol; dichloromethane / 0 °C
5.1: sodium hydride / tetrahydrofuran / 0 °C
5.2: 0 - 20 °C
6.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 80 °C
7.1: LiDBB / tetrahydrofuran / -78 °C
8.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 20 °C
9.1: n-butyllithium / tetrahydrofuran / 20 °C
9.2: -78 - 0 °C
10.1: pyridine; Dess-Martin periodane / dichloromethane / 0 - 20 °C
11.1: diisobutylaluminium hydride / dichloromethane / -78 °C
12.1: N-chloro-succinimide; water; silver nitrate / acetonitrile / 20 °C
With
pyridine; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; N-chloro-succinimide; n-butyllithium; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; water; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; silver nitrate; dimethyl sulfoxide; triethylamine; zinc(II) chloride;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; benzene;
6.1: Barton-McCombie deoxygenation / 8.1: Parikh-Doering oxidation;
DOI:10.1016/j.tetlet.2012.06.005