Multi-step reaction with 14 steps
1.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere
2.1: tetrahydrofuran / 12 h / Inert atmosphere; Reflux
3.1: lithium borohydride / ethanol / 4 h / Inert atmosphere
4.1: palladium 10% on activated carbon; ammonium formate / methanol / 12.5 h / Inert atmosphere
5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / Inert atmosphere
6.1: sodium hydride / N,N-dimethyl-formamide; tetrahydrofuran; mineral oil / 2 h / 0 - 60 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere
8.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere
9.1: copper(II) sulfate / toluene / 16 h / 20 °C / Inert atmosphere
10.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; chlorobenzene / 0.5 h / 20 - 110 °C / Inert atmosphere
11.1: hydrogenchloride / Inert atmosphere
12.1: N-ethyl-N,N-diisopropylamine; pivaloyl chloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
12.2: 0.5 h / 0 - 20 °C / Inert atmosphere
13.1: (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II) / toluene / 2 h / Reflux; Inert atmosphere
13.2: 5 h / 20 °C
13.3: 4 h / 0 °C / Inert atmosphere
14.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere
14.2: 1.25 h / 0 °C / Inert atmosphere
With
hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium borohydride; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); palladium 10% on activated carbon; tetrabutyl ammonium fluoride; ammonium formate; pivaloyl chloride; sodium hydride; Dess-Martin periodane; copper(II) sulfate; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; chlorobenzene; toluene; mineral oil;
10.1: |Grignard Reaction;
DOI:10.1021/ol400469w