Multi-step reaction with 9 steps
1.1: diisobutylaluminium hydride / hexane; toluene / 2 h / -78 °C / Inert atmosphere
2.1: sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere
3.1: pentane; diethyl ether / 0.75 h / -78 - 0 °C / Inert atmosphere
4.1: pyridine hydrogenfluoride; THF-pyridine / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere
4.2: 1 h / 20 °C / Inert atmosphere
5.1: acetic acid / methanol / 26 h / 0 °C / Inert atmosphere
6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; aq. phosphate buffer; acetone / 2 h / 20 °C / pH 7 / Inert atmosphere
7.1: sodium periodate / tetrahydrofuran; aq. phosphate buffer / 0.5 h / 20 °C / pH 7 / Inert atmosphere
8.1: hydroxylamine hydrochloride; pyridine / ethanol / 1 h / 0 °C / Inert atmosphere
9.1: pyridine; N-ethyl-N,N-diisopropylamine; N-chloro-succinimide / chloroform / 44.75 h / 20 - 60 °C / Inert atmosphere
With
pyridine; sodium periodate; N-chloro-succinimide; osmium(VIII) oxide; THF-pyridine; hydroxylamine hydrochloride; sulfur trioxide pyridine complex; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; chloroform; dimethyl sulfoxide; acetone; toluene; pentane;
DOI:10.1021/ol302691j