Multi-step reaction with 23 steps
1.1: 1,1,1,3,3,3-hexachloro-propan-2-one; triphenylphosphine / dichloromethane / 0.08 h / 0 °C
2.1: diisobutylaluminium hydride / hexane; toluene / 0.17 h / -78 °C
3.1: pyridine / 0.5 h / 20 °C
4.1: iodonium(di-γ-collidine) perchlorate / dichloromethane / 4 h / 20 °C
5.1: triethyl borane; tri-n-butyl-tin hydride / tetrahydrofuran / 1 h / -78 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.17 h / 20 °C
8.1: tetrahydrofuran / 0.17 h / 0 °C
9.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C
10.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.17 h / -78 °C
11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
12.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
12.2: 2 h / -78 - 20 °C
13.1: tetrabutyl ammonium fluoride / 2 h / 20 °C
14.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
15.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
16.1: sodium azide; ammonium chloride / methanol; water / 10 h / Reflux
17.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C
18.1: copper(II) bis(trifluoromethanesulfonate) / acetonitrile / 3 h / 20 °C / Molecular sieve
19.1: sodium tetrahydroborate; nickel(II) chloride hexahydrate / tetrahydrofuran; methanol / 3.17 h / 0 - 20 °C
20.1: lithium triethylborohydride / tetrahydrofuran / 1.5 h / 0 - 40 °C
21.1: naphthalene; lithium / tetrahydrofuran / 1 h / -78 - 20 °C
22.1: dichloromethane / 4 h / 20 °C
23.1: pyridine; p-toluenesulfonyl chloride / dichloromethane / 12 h / 20 °C
With
pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; disodium hydrogenphosphate; n-butyllithium; sodium azide; naphthalene; nickel(II) chloride hexahydrate; 1,1,1,3,3,3-hexachloro-propan-2-one; triethyl borane; iodonium(di-γ-collidine) perchlorate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; lithium; copper(II) bis(trifluoromethanesulfonate); diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane;
In
tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
14.1: intramolecular Diels-Alder reaction;
DOI:10.1039/c1cc16468f