Multi-step reaction with 13 steps
1.1: o-xylene / 20 h / 165 °C / Inert atmosphere
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C
2.2: NaBO3*4H2O / 3 h / 20 °C
3.1: pyridine; dmap / dichloromethane / 1 h / 0 - 20 °C
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 10 h / 20 °C
5.1: pyridine; tributylphosphine / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
6.1: dihydrogen peroxide / dichloromethane; water / 29 h / 20 °C / pH 7 / aq. phosphate buffer
7.1: cerium(III) chloride heptahydrate; oxalic acid / acetonitrile / 2 h / 20 °C
8.1: dichloromethane / 1.5 h / 20 °C
9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C
11.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
12.1: ammonium acetate; sodium sulfate / 19 h / 75 °C
13.1: copper(I) trifluoromethanesolfonate toluene complex; N-[2-(diphenylphosphino)benzylidene]-L-Tle-L-Tyr(OBn)-NEt2 / toluene / 0.17 h / -30 °C / Inert atmosphere
13.2: -30 - 0 °C / Inert atmosphere
With
pyridine; dmap; copper(I) trifluoromethanesolfonate toluene complex; tributylphosphine; cerium(III) chloride heptahydrate; N-[2-(diphenylphosphino)benzylidene]-L-Tle-L-Tyr(OBn)-NEt2; ammonium acetate; tetrabutyl ammonium fluoride; dihydrogen peroxide; oxalic acid; Dess-Martin periodane; sodium sulfate; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran; dichloromethane; o-xylene; water; toluene; acetonitrile;
2.1: Hydroboration reaction;
DOI:10.1002/anie.201104681