Multi-step reaction with 11 steps
1.1: t-butyldimethylsiyl triflate; 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
2.1: potassium tert-butylate / tetrahydrofuran / 20 °C
2.2: 4 h / 30 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 20 h / 50 °C
3.2: 1 h / 0 - 25 °C
4.1: 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 0 °C / Molecular sieve
4.2: 0 - 20 °C
5.1: perchloric acid / water / 1 h / 100 °C
6.1: potassium hydroxide / tert-butyl alcohol; water / 17 h / 30 °C
7.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -70 °C
8.1: n-butyllithium / tetrahydrofuran / 0.08 h / 20 °C
8.2: 9.5 h / -25 °C
9.1: pyridine hydrogenfluoride / tetrahydrofuran / 3 h / 20 °C
10.1: calcium carbonate / methanol / 0.33 h / -80 °C
10.2: 0.33 h / -80 °C
11.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
With
2,6-dimethylpyridine; dmap; n-butyllithium; perchloric acid; t-butyldimethylsiyl triflate; potassium tert-butylate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; 9-bora-bicyclo[3.3.1]nonane; calcium carbonate; potassium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
2.1: |Wittig Olefination / 2.2: |Wittig Olefination / 4.2: |Ley Oxidation;
DOI:10.1002/chem.201301186