Multi-step reaction with 11 steps
1.1: sodium hydride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
1.2: 24 h / 25 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C
2.2: 20 °C
3.1: lithium chloride; tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,2-dimethoxyethane / 2 h / 80 °C
4.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / 0 °C
5.1: tetrahydrofuran / 1 h / 0 °C
6.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H42N2; potassium tert-butylate; hydrogen / propan-1-ol / 0.25 h / 25 °C / 4560.31 Torr / Inert atmosphere; Autoclave
7.1: trimethylpyruvic acid / 5,5-dimethyl-1,3-cyclohexadiene / 5 h / 140 °C
8.1: ozone / methanol / 3 h / -78 °C
9.1: sodium tetrahydroborate / methanol; water / 1 h / 25 °C / Inert atmosphere
10.1: sodium hydroxide; water / methanol / 1 h / 25 °C
11.1: triethylamine; chloroformic acid ethyl ester / chloroform / 0.5 h / -15 °C
With
sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium(0); bis(1,5-cyclooctadiene)diiridium(I) dichloride; C37H42N2; potassium tert-butylate; water; hydrogen; isopropylmagnesium chloride; chloroformic acid ethyl ester; sodium hydride; sodium carbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; trimethylpyruvic acid; lithium chloride; sodium hydroxide;
In
tetrahydrofuran; methanol; propan-1-ol; 1,2-dimethoxyethane; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; chloroform; water;
7.1: |Johnson-Claisen Rearrangement;
DOI:10.1021/ol302842h