Multi-step reaction with 19 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere
2.1: diethylaluminium chloride / dichloromethane / 14 h / -78 °C / Inert atmosphere
3.1: tert-butyl alcohol; lithium; ammonia / tetrahydrofuran / 6 h / -78 °C
4.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / 0 °C / Inert atmosphere
5.1: 5,5-dimethyl-1,3-cyclohexadiene / 13 h / 160 °C / Sealed tube; Inert atmosphere
6.1: iodine / tetrahydrofuran; water / 0 - 20 °C
7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 5 h / Reflux; Inert atmosphere
8.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere
9.1: diisobutylaluminium hydride / dichloromethane / 0.67 h / -78 °C / Inert atmosphere
10.1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; methanol / -78 - -40 °C / Inert atmosphere
11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
12.1: potassium tert-butylate / tetrahydrofuran; toluene / 1 h / 20 °C / Inert atmosphere
12.2: 4 h / 100 °C / Inert atmosphere
13.1: sodium hydride; 1H-imidazole / tetrahydrofuran / 3 h / Reflux; Inert atmosphere
13.2: 1 h / Reflux; Inert atmosphere
14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / Reflux
15.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.33 h / 0 °C
16.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere
16.2: MoO5(py)(HMPA) / 1.5 h / -25 °C / Inert atmosphere
17.1: tetrahydrofuran / 0.33 h / 0 °C
18.1: (triphenylphosphine)gold(I) chloride; silver tetrafluoroborate / dichloromethane / 20 °C
19.1: osmium(VIII) oxide / tetrahydrofuran; pyridine / 0 - 20 °C
With
1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; osmium(VIII) oxide; silver tetrafluoroborate; samarium diiodide; (triphenylphosphine)gold(I) chloride; cerium(III) chloride heptahydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; iodine; diethylaluminium chloride; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; tert-butyl alcohol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; pyridine; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
3.1: |Birch Reduction / 4.1: |Luche Cerium Reduction / 5.1: |Eschenmoser-Claisen Rearrangement / 12.1: |Wittig Olefination / 13.2: |Barton-McCombie Deoxygenation;
DOI:10.1021/ol500623w