Multi-step reaction with 12 steps
1: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -30 °C
2: Dess-Martin periodane / dichloromethane
3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran; water
4: trimethylaluminum / dichloromethane; water / -50 °C
5: toluene-4-sulfonic acid / benzene / Reflux
6: diisobutylaluminium hydride / tetrahydrofuran / 0 °C
7: titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate / dichloromethane / -30 °C
8: copper(l) cyanide / diethyl ether / -50 - -30 °C
9: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane
10: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol
11: diethyl ether / 0 °C
12: N-ethyl-N,N-diisopropylamine; sodium iodide / 1,2-dimethoxyethane / Reflux
With
titanium(IV) isopropylate; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; diethyl (2R,3R)-tartrate; [bis(acetoxy)iodo]benzene; trimethylaluminum; copper(l) cyanide; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;
1: Katsuki-Sharpless epoxidation / 2: Dess-Martin oxidation / 2: Wittig reaction / 7: Katsuki-Sharpless epoxidation;
DOI:10.3987/COM-10-12106