Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10.5 h / 23 °C / Inert atmosphere
2.1: methanol; hexane; benzene / 0.08 h / 23 °C / Inert atmosphere
2.2: 0.5 h
3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
3.2: 1 h / -78 °C / Inert atmosphere
4.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere
4.2: 18 h / 23 °C / Inert atmosphere
5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 0.33 h / 0 - 23 °C
6.1: triethylamine / acetonitrile / 0.5 h / 0 - 23 °C
7.1: (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine / dichloromethane / 20 h / 23 °C
8.1: phosphorous acid trimethyl ester / methanol / 36 h
9.1: dmap / dichloromethane / 2 h / 23 °C
10.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C
11.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 12 h / 23 °C / Darkness
12.1: triethylamine / tetrahydrofuran / 0.67 h / 0 °C
13.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere
13.2: 2 h / -75 - 0 °C / Inert atmosphere
14.1: hydrogen fluoride; water / acetonitrile / 60 h / 23 °C / Inert atmosphere
15.1: palladium; hydrogen / methanol; tetrahydrofuran / 2 h / 23 °C / 760.05 Torr
15.2: Inert atmosphere
With
dmap; n-butyllithium; carbon tetrabromide; N,N,N,N,-tetramethylethylenediamine; 2-iodoxybenzoic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; water; hydrogen; lithium trifluoromethanesulfonate; palladium; acetic acid; (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; phosphorous acid trimethyl ester;
In
tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; benzene;
13.1: |Michael Addition / 13.2: |Dieckmann Condensation;