Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve
1.2: 16 h / -20 °C / Molecular sieve
2.1: copper(l) iodide / diethyl ether / 0.33 h / -40 °C
2.2: 20 °C
3.1: 1H-imidazole / dichloromethane / 0 - 35 °C
4.1: di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C
4.2: 27 h / 20 - 35 °C
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C
6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 4 h / 0 - 20 °C
7.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C
7.2: 6 h / 20 °C
8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 4 h / 20 °C / 760.05 Torr
9.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 0.25 h / 0 °C
9.2: 6 h / 0 - 35 °C
10.1: pyridine hydrogenfluoride / acetonitrile / 12 h / 0 °C
11.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 5 h / 0 - 20 °C
With
1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; di-isopropyl azodicarboxylate; 2,4,6-trichlorobenzoyl chloride; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; pyridine hydrogenfluoride; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
1.1: |Sharpless Asymmetric Epoxidation / 1.2: |Sharpless Asymmetric Epoxidation / 4.1: |Mitsunobu Displacement / 4.2: |Mitsunobu Displacement;
DOI:10.1055/s-0039-1691503