Multi-step reaction with 13 steps
1.1: trans-RuCl2-[(R)-xylbinap][(R)-daipen]; hydrogen / 37503.8 Torr
2.1: bromine / methanol; diethyl ether / 1.08 h / -78 - -30 °C / Inert atmosphere
2.2: 0.08 h / 23 °C / Inert atmosphere
3.1: L-Selectride / tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere
4.1: tetrahydrofuran / 7.08 h / -78 - -25 °C / Inert atmosphere
5.1: tetrakis(triphenylphosphine) palladium(0); lithium chloride / tetrahydrofuran / 23 - 80 °C / Inert atmosphere
6.1: water / tetrahydrofuran; water; pentane / Inert atmosphere
7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone; tert-butyl alcohol / 73 h / 0 - 23 °C / Inert atmosphere; Cooling with ice
8.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
9.1: sodium periodate; ruthenium trichloride / tetrachloromethane; water; acetonitrile / 1 h / Inert atmosphere; Cooling with ice
10.1: N,N-dimethyl-formamide / 23 - 50 °C / Inert atmosphere
11.1: sulfuric acid; water / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere
12.1: acetic acid / water / 2 h / 95 °C / Inert atmosphere
13.1: diethylamino-sulfur trifluoride / tetrahydrofuran / 0.33 h / -40 °C / Inert atmosphere
With
ruthenium trichloride; sodium periodate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium(0); thionyl chloride; diethylamino-sulfur trifluoride; sulfuric acid; trans-RuCl2-[(R)-xylbinap][(R)-daipen]; water; hydrogen; bromine; L-Selectride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; lithium chloride;
In
tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/ol202315m