Multi-step reaction with 14 steps
1.1: tert.-butyl lithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere
1.2: brine
2.1: Burgess Reagent / tetrahydrofuran / 20 - 50 °C / Inert atmosphere
3.1: dichloromethane / 0.33 h / 0 °C / Inert atmosphere
4.1: sodium hydroxide / methanol; water / 0.33 h / 20 °C
5.1: N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium carbonate / dichloromethane / 20 °C / Inert atmosphere
6.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere
7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere
7.2: brine
8.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve
9.1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
10.1: sodium cyanoborohydride / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 24 h / 66 °C / Inert atmosphere
11.1: ammonia / methanol; water / 6 h / 66 °C
11.2: 0 °C / pH 2
12.1: pyridine / acetonitrile / 0.5 h / 0 °C / Inert atmosphere
13.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 100 °C / Inert atmosphere
14.1: N-ethyl-N,N-diisopropylamine; sodium iodide / 1,2-dimethoxyethane / 24 h / Reflux
With
pyridine; 1H-imidazole; tert.-butylhydroperoxide; N-chloro-succinimide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; bis(acetylacetonate)oxovanadium; Burgess Reagent; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; ammonia; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium iodide; sodium hydroxide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
1.1: Barbier type cyclization / 8.1: Sharpless epoxidation;
DOI:10.1021/ol300390k