Multi-step reaction with 11 steps
1.1: triethylamine / chloroform / 1 h / 0 - 20 °C
2.1: pyrrolidine / benzene / 20 °C / Inert atmosphere; Dean-Stark; Reflux
2.2: 70 °C / Inert atmosphere; Dean-Stark
3.1: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C
3.2: 0.33 h / 20 °C
3.3: Bargellini Reaction / 0 - 45 °C
4.1: diazomethyl-trimethyl-silane / acetonitrile; methanol / 0 - 20 °C
5.1: ChiralPak AD-5cm 20μm / hexane; isopropyl alcohol / 25 °C / Resolution of racemate
6.1: trimethylsilyl iodide / dichloromethane / 2 h / 20 °C
7.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 45 °C
8.1: potassium hydroxide / ethanol / 2.5 h / 65 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 - 40 °C
10.1: osmium(VIII) oxide; pyridine; sodium periodate / water; tert-butyl alcohol; 1,4-dioxane / 18 h / 20 °C
11.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C
With
pyrrolidine; pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; trimethylsilyl iodide; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; potassium hydroxide; sodium hydroxide; diazomethyl-trimethyl-silane;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; chloroform; water; isopropyl alcohol; acetonitrile; tert-butyl alcohol; benzene;
3.1: |Bargellini Reaction / 3.2: |Bargellini Reaction;
DOI:10.1021/ml500019s