Multi-step reaction with 20 steps
1.1: methanol; potassium carbonate / 1 h / 0 °C / Inert atmosphere
1.2: 0 °C / pH 3
2.1: 10% palladium on activated carbon; hydrogen / methanol / 10 h / 20 °C / 760.05 Torr
3.1: N-Bromosuccinimide / acetonitrile / 1 h / 0 °C / Inert atmosphere
4.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
5.1: methanol; acetyl chloride / dichloromethane / 5 h / 20 °C / Inert atmosphere
6.1: lithium hydroxide monohydrate / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere; Molecular sieve
6.2: 20 h / 20 °C / Inert atmosphere; Molecular sieve
7.1: sodium hydrogencarbonate / dichloromethane; water / 2 h / 0 °C
8.1: tin(II) bromide / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere
9.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0 - 20 °C
9.2: 0 °C
10.1: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / 3.5 h / 20 °C / Inert atmosphere
11.1: dichloromethane / 22 h / 20 °C / Inert atmosphere
12.1: magnesium sulfate; toluene-4-sulfonic acid / toluene / 12 h / 90 °C / Inert atmosphere
13.1: phenyltrimethylammonium tribromide / acetonitrile / 20 - 60 °C / Inert atmosphere; Molecular sieve
14.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
15.1: 3,3-dimethyldioxirane / methanol; acetone / 2 h / 0 °C / Inert atmosphere
16.1: CSA / 0 - 20 °C / Inert atmosphere
17.1: sodium cyanoborohydride; trifluoroacetic acid / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere
18.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
19.1: toluene-4-sulfonic acid / methanol / 5 h / Inert atmosphere; Reflux
20.1: potassium trimethylsilonate / acetonitrile / 2.5 h / 0 - 50 °C / Inert atmosphere
20.2: 0 °C
With
methanol; N-Bromosuccinimide; (triphenylphosphine)gold(I) chloride; lithium hydroxide monohydrate; 10% palladium on activated carbon; potassium trimethylsilonate; hydrogen; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; phenyltrimethylammonium tribromide; tin(II) bromide; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium sulfate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetyl chloride; trifluoroacetic acid; potassium iodide; lithium hydroxide; silver(I) triflimide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
13.1: Friedel Crafts alkylation;
DOI:10.1021/jo100788j