Multi-step reaction with 11 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / -95 - -78 °C / Inert atmosphere
2.1: tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 24 h / -40 - -30 °C / Inert atmosphere
3.1: camphor-10-sulfonic acid / dichloromethane; methanol / 4 h / 0 - 20 °C / Inert atmosphere
4.1: camphor-10-sulfonic acid / dichloromethane; methanol / 2 h / 0 °C / Inert atmosphere
5.1: Proton-sponge / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / dichloromethane; toluene / -10 °C / Inert atmosphere
7.1: Dess-Martin periodane / dichloromethane; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere
9.1: triethylamine; dmap / dichloromethane / 2 h / 0 °C / Inert atmosphere
10.1: tin(II) trifluoromethanesulfonate; 1-ethyl-piperidine / dichloromethane / 4.5 h / -50 °C / Inert atmosphere
10.2: 12 h / -78 °C / Inert atmosphere
11.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
With
1-ethyl-piperidine; 2,6-dimethylpyridine; dmap; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; methanol; dichloromethane; acetic acid; toluene; acetonitrile; tert-butyl alcohol;
1.1: |Mukaiyama Aldol Addition;
DOI:10.1021/ol5008179