Multi-step reaction with 11 steps
1.1: CrCl(C6H2(O)(C10H15)(CH3)(CHNC9H8O)) / 20.5 h / 20 °C / Molecular sieve
2.1: potassium carbonate / methanol / 0.5 h / 20 °C
2.2: 20 °C
3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.67 h / -20 °C
4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C
5.1: camphor-10-sulfonic acid / methanol; dichloromethane / 1 h / 0 °C
6.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
7.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C
8.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C
8.2: 0.67 h
8.3: 14 h / 20 °C
9.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / methanol; dichloromethane / 1.5 h / 0 °C
10.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 27 h / 0 - 20 °C / Molecular sieve
11.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2.5 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; tetrapropylammonium perruthennate; CrCl(C6H2(O)(C10H15)(CH3)(CHNC9H8O)); cerium(III) chloride heptahydrate; camphor-10-sulfonic acid; potassium tert-butylate; iodine; sodium hydrogencarbonate; potassium carbonate; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol301278e