Multi-step reaction with 12 steps
1.1: camphor-10-sulfonic acid / methanol; dichloromethane / 5 h / 0 °C
2.1: sulfur trioxide pyridine complex; triethylamine / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C
3.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C
3.2: 2 h / -78 - 0 °C
4.1: tetrahydrofuran / 0.5 h / 20 °C
5.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 2 h / 0 - 20 °C
6.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 1.5 h / 20 °C
6.2: 1 h / 20 °C
7.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere
8.1: titanium(IV) isopropylate; (-)-diethyl tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve
8.2: -20 °C / Molecular sieve
9.1: N-chloro-succinimide; triphenylphosphine; methyloxirane / dichloromethane / 0.75 h / 0 °C
10.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -40 °C / Inert atmosphere
11.1: N-iodo-succinimide; silver nitrate / acetone / 1 h / 0 °C
12.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 6.5 h / 0 - 20 °C
With
titanium(IV) isopropylate; N-chloro-succinimide; N-iodo-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (-)-diethyl tartrate; camphor-10-sulfonic acid; 2-nitrobenzenesulfonyl hydrazide; potassium tert-butylate; dihydrogen peroxide; sulfur trioxide pyridine complex; diisobutylaluminium hydride; silver nitrate; triethylamine; triphenylphosphine; methyloxirane; sodium hydroxide; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; acetone;
8.1: Sharpless epoxidation / 8.2: Sharpless epoxidation;
DOI:10.1021/ja305864z