Multi-step reaction with 11 steps
1.1: sodium tetrahydroborate / water; tetrahydrofuran / 20 h / 0 - 20 °C
2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C
2.2: 20 h / 20 °C
3.1: diisobutylaluminium hydride / toluene; diethyl ether / 0.25 h / -40 °C / Inert atmosphere
4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 15 h / 0 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / Cooling with ice
6.1: periodic acid dihydrate / diethyl ether / 0.25 h
7.1: tetrakis(triphenylphosphine) palladium(0); pyrrolidine / tetrahydrofuran / 20 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere
9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 20 °C
9.2: 2 h / 20 °C
10.1: diisopropylamine; n-butyllithium / hexane; toluene / 0.5 h / -78 °C
10.2: 0.33 h / -78 - 0 °C
10.3: 9 h / 60 °C
11.1: (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate / isopropyl alcohol / 1.5 h / 70 °C
With
pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; periodic acid dihydrate; carbon tetrabromide; (triphenylphosphine)gold(I)bis(trifluoromethanesulfonyl)imidate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; isopropyl alcohol; toluene;
DOI:10.1039/c3ob40692j