Multi-step reaction with 10 steps
1.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 1.7 h / -10 - 20 °C / Inert atmosphere
2.2: 1 h / 20 °C / Inert atmosphere
3.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 110 °C / Inert atmosphere
3.2: 16 h / 0 - 20 °C
4.1: iron(III) chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
5.1: manganese(IV) oxide / dichloromethane / 13 h / 20 °C / Inert atmosphere
6.1: caesium carbonate / methanol; tetrahydrofuran; water / 11 h / 0 °C / Inert atmosphere
7.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 0 °C
7.2: 6.6 h / 0 °C
8.1: ozone / dichloromethane / 0.25 h / -78 °C
8.2: 0.17 h / -78 °C / Inert atmosphere
9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere
10.1: triethylamine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7.5 h / 0 °C / Inert atmosphere
10.2: 0.67 h / -78 °C / Molecular sieve
With
manganese(IV) oxide; iron(III) chloride; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium carbonate; caesium carbonate; ozone; acetic acid; lithium tri-t-butoxyaluminum hydride; triethylamine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
3.1: |Barton-McCombie Deoxygenation / 10.2: |Mukaiyama Aldol Addition;
DOI:10.1002/asia.201300362