Multi-step reaction with 15 steps
1: hydrogenchloride / tetrahydrofuran; water / 2.5 h / 20 °C / Inert atmosphere; Heating
2: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere
3: toluene-4-sulfonic acid / benzene / Inert atmosphere; Reflux
4: tetrahydrofuran / Inert atmosphere
5: pyridine; thionyl chloride / dichloromethane / Inert atmosphere
6: dihydrogen peroxide; 9-borabicyclo[3.3.1]nonane; sodium hydroxide / Inert atmosphere
7: 1H-imidazole; iodine; triphenylphosphine / Inert atmosphere
8: tetra-(n-butyl)ammonium iodide; sodium hydroxide / water; benzene / 2.5 h / 100 °C / Inert atmosphere
9: naphthalene; sodium / 1,2-dimethoxyethane / 2.5 h / 100 °C / Inert atmosphere
10: dmap / dichloromethane / Inert atmosphere
11: hydrogenchloride / Inert atmosphere
12: oxone; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate / Inert atmosphere
13: potassium hydroxide / methanol / Inert atmosphere; Reflux
14: Jones reagent / Inert atmosphere
15: sodium tetrahydroborate / ethanol / 0 °C / Inert atmosphere
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; sodium tetrahydroborate; Jones reagent; thionyl chloride; oxone; Shi's ketone; naphthalene; dihydrogen peroxide; iodine; tetra(n-butyl)ammonium hydrogensulfate; sodium; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; 9-borabicyclo[3.3.1]nonane; triphenylphosphine; pyridinium chlorochromate; potassium hydroxide; sodium hydroxide;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; benzene;
1: Helquist annulation reaction / 12: Shi asymmetric epoxidation reaction / 14: Jones oxidation;
DOI:10.1021/jo1023188