Multi-step reaction with 12 steps
1.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine / dichloromethane / 0 - 25 °C
2.1: tetrahydrofuran; diethyl ether / -78 - 0 °C
3.1: tert.-butyl lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane / 0.08 h / -78 °C
3.2: 1 h / -78 °C
4.1: water; iodine; sodium hydrogencarbonate / acetonitrile / 0.08 h / 0 - 25 °C
5.1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 - 0 °C
6.1: manganese(IV) oxide / dichloromethane / 3 h / 25 °C
7.1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-amino-1,2-diphenylethyl)thiourea; acetic acid / toluene / 72 h / 0 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
9.1: phenylborondichloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -78 °C
9.2: 1.5 h / -78 °C
10.1: diethyl methoxy borane / tetrahydrofuran; methanol / 0.5 h / -78 °C
10.2: -78 - 0 °C
11.1: (1S)-10-camphorsulfonic acid / dichloromethane / 1 h / 25 °C
12.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C
With
2,6-dimethylpyridine; manganese(IV) oxide; sodium tetrahydroborate; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-amino-1,2-diphenylethyl)thiourea; diethyl methoxy borane; phenylborondichloride; (1S)-10-camphorsulfonic acid; water; iodine; tert.-butyl lithium; sulfur trioxide pyridine complex; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene; acetonitrile; pentane;
9.1: Aldol addition / 9.2: Aldol addition;
DOI:10.1021/ol2024289