Multi-step reaction with 13 steps
1.1: triethylamine / dichloromethane / 0 - 20 °C
2.1: tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 48 h / 60 °C
3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C
4.1: 1-methyl-pyrrolidin-2-one; titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C
4.2: 1 h
5.1: methanol; lithium borohydride / tetrahydrofuran; diethyl ether / 0 - 20 °C
6.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h
6.2: 8 h / -78 - 20 °C
7.1: triethylamine / dichloromethane / 0 - 20 °C
8.1: lithium triethylborohydride / tetrahydrofuran / 20 °C
8.2: 0 °C
9.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux
10.1: diethyl ether / -78 °C
11.1: 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / -78 °C
12.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 0 °C
With
2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; methanol; lithium borohydride; Hoveyda-Grubbs catalyst second generation; 4,4'-di-tert-butylbiphenyl; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; lithium; diisobutylaluminium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
12.1: Parikh-Doering oxidation;
DOI:10.1021/ol300785c
