Multi-step reaction with 8 steps
1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.17 h / cooling
1.2: tetrahydrofuran; hexane / 6 h
2.1: 92 percent / p-toluenesulfonic acid monohydrate / acetone
3.1: BF3*OEt2 / 0.17 h / cooling
3.2: 68 percent / lead(IV) acetate / benzene
4.1: 54 percent / borane dimethyl sulfide complex / tetrahydrofuran / 20 °C
5.1: Dess-Martin periodinane / CH2Cl2 / 20 °C
6.1: toluene / 0.02 h
6.2: L,R,R-Jacobsen peptide / toluene / 49 h / -78 - 20 °C
7.1: hydrogen chloride (gas) / 8 h / 20 °C
8.1: N,N'-dimethylbarbituric acid / tetrakis(triphenylphosphine)palladium(0) / CH2Cl2 / 3 h / 35 °C
With
hydrogenchloride; 1,3-dimethylbarbituric acid; dimethylsulfide borane complex; boron trifluoride diethyl etherate; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; hexane; dichloromethane; acetone; toluene;
5.1: Dess-Martin oxidation / 6.2: Jacobsen-Strecker asymmetric reaction / 7.1: Pinner reaction;
DOI:10.1021/ol049619m