Multi-step reaction with 13 steps
1.1: LDA / tetrahydrofuran; hexane / 0.75 h / -78 °C
1.2: 89 percent / tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C
2.1: 95 percent / LiAlH4 / diethyl ether / 12 h / Heating
3.1: (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
4.1: 4.835 g / sodium cyanoborohydride; AcOH / methanol / 2 h / 20 °C
5.1: 96 percent / TEA / CH2Cl2 / 19 h / 20 °C
6.1: O3 / CH2Cl2 / 0.25 h / -78 °C
6.2: 34 percent / PPh3 / CH2Cl2 / -78 - 20 °C
7.1: 54 percent / t-BuOK / 12 h / 20 °C
8.1: TFA / CH2Cl2 / 20 °C
9.1: 97 mg / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C
10.1: (S)-(-)-α,α-diphenyl-2-pyrrolidinemethanol; BH3*SMe2 / tetrahydrofuran / 45 - 50 °C
11.1: TEA / CH2Cl2
12.1: I2 / CH2Cl2 / 0.25 h / 0 °C
12.2: 75 percent / CH2Cl2 / 1 h / 0 °C
13.1: 96 percent / TFA / CH2Cl2 / 20 °C
With
lithium aluminium tetrahydride; oxalyl dichloride; (S)-diphenylprolinol; dimethylsulfide borane complex; TEA; potassium tert-butylate; iodine; sodium cyanoborohydride; ozone; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;
3.1: Swern oxidation / 9.1: Swern oxidation;
DOI:10.1021/ol035564x