Multi-step reaction with 16 steps
1.1: triethylamine / dichloromethane; water / 1 h / 20 °C
2.1: dimethyl sulfoxide / 30 h / 60 °C
3.1: pyridinium p-toluenesulfonate / methanol / 4 h / Reflux
4.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C / Molecular sieve
5.1: dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C
6.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; tert-butyl alcohol; acetone / 20 h / 20 °C
6.2: 4 h / 20 °C
7.1: pyridine / 16 h / 20 °C
8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 20 °C
9.1: sodium hydroxide / ethanol; water / 12 h / 60 °C
10.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C
11.1: formic acid / diethyl ether / -5 °C
12.1: pyridinium chlorochromate / dichloromethane; diethyl ether / 20 °C / Molecular sieve
13.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -70 °C
13.2: -70 - 20 °C
14.1: acetic acid; water / tetrahydrofuran / 20 °C
15.1: tetrahydrofuran; hexane / -70 °C
16.1: α,α,α-trifluorotoluene; magnesium oxide / 72 h / 85 °C
With
pyridine; 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; formic acid; α,α,α-trifluorotoluene; water; pyridinium p-toluenesulfonate; magnesium oxide; potassium hexamethylsilazane; acetic acid; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; sodium hydroxide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; tert-butyl alcohol;
13.1: |Wittig-Horner Reaction;
DOI:10.1271/bbb.120317
DOI:10.1271/bbb.120317