Multi-step reaction with 8 steps
1.1: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
2.1: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / Inert atmosphere; Schlenk technique
3.1: tetrahydrofuran; diethyl ether / 0.25 h / -78 - 0 °C / Inert atmosphere; Schlenk technique
4.1: hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); potassium osmate; potassium carbonate; methanesulfonamide / water; tert-butyl alcohol / 18 h / 20 °C / Inert atmosphere; Schlenk technique
5.1: iodine; silver trifluoroacetate / chloroform / 1.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
6.1: N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide / 24 h / 100 °C / 760.05 Torr / Schlenk technique
7.1: triethylamine; dmap / dichloromethane / 0.25 h / 0 °C / Inert atmosphere; Schlenk technique
8.1: boron trifluoride diethyl etherate / dichloromethane / 0.05 h / -78 °C / Inert atmosphere; Schlenk technique
8.2: 1.5 h / -78 °C / Inert atmosphere; Schlenk technique
With
dmap; potassium osmate; tetrakis(triphenylphosphine) palladium(0); 18-crown-6 ether; methanesulfonamide; boron trifluoride diethyl etherate; potassium tert-butylate; iodine; palladium diacetate; silver trifluoroacetate; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); ruphos;
In
tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: |Wittig Olefination / 2.1: |Suzuki Coupling / 4.1: |Sharpless Dihydroxylation / 8.1: |Mukaiyama Aldol Addition / 8.2: |Mukaiyama Aldol Addition;
DOI:10.1021/ol402191t