Multi-step reaction with 14 steps
1.1: sodium methylate / methanol / 0.17 h / 20 °C
2.1: toluene-4-sulfonic acid / methanol / 3 h / 20 °C
3.1: boron trifluoride diethyl etherate; 2,2-dimethoxy-propane / 0.5 h / 20 °C
4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C
4.2: 3 h / -78 °C
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / -40 °C
6.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1 h / 0 °C
7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; tert-butyl alcohol / 24 h / 20 °C
8.1: triethylamine / dichloromethane / 24 h / 0 - 20 °C
9.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C
9.2: 72 h / 20 °C
10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 - 20 °C
11.1: pyridine / 0.67 h / 0 °C
12.1: sodium hydrogencarbonate / dimethyl sulfoxide / 8 h / 60 °C
13.1: toluene-4-sulfonic acid / methanol / 6 h / 20 °C
14.1: silver(l) oxide / ethyl acetate / 16 h / 20 °C
With
pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; n-butyllithium; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,2-dimethoxy-propane; silver(l) oxide;
In
tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; mineral oil; tert-butyl alcohol;
5.1: |Wittig-Horner Reaction;
DOI:10.3762/bjoc.8.210