Multi-step reaction with 8 steps
1: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 h
2: 1) LDA / 1) THF, -78 deg C, 30 min, 2) THF, -78 deg C, 2 h
3: acetonitrile / 48 h / 20 °C
4: 14.5 g / NaBH4 / methanol / 4 h / 0 °C
5: 100 percent / H2, PtO2 / ethanol / 3 h / 20 °C
6: 1) mCPBA / 1) CH2Cl2, 0 deg C to 20 deg C, 2 h, 2) CH3CN, reflux, 2 h
7: 82 percent / sodium naphthalide / tetrahydrofuran / 2 h / Ambient temperature
8: 94 percent / N-chlorosuccinimide / CH2Cl2 / 0.5 h / 20 °C
With
platinum(IV) oxide; sodium tetrahydroborate; N-chloro-succinimide; hydrogen; sodium naphthalenide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(98)00270-1