Multi-step reaction with 13 steps
1.1: 90 percent / p-TsOH / benzene / 4 h / 80 °C
2.1: Li; tert-butyl alcohol / liquid ammonia; diethyl ether / 0.5 h / -78 - -45 °C
2.2: isoprene / liquid ammonia; diethyl ether / -78 - -45 °C
2.3: 87 percent / diethyl ether / 2 h / -78 - 0 °C
3.1: NaH / hexamethylphosphoric acid triamide / 3 h / 25 °C
3.2: 95 percent / hexamethylphosphoric acid triamide / 2 h / 25 °C
4.1: Li / liquid ammonia; 1,2-dimethoxy-ethane / 0.33 h / -78 - -33 °C
4.2: 61 percent / 1,2-dimethoxy-ethane; liquid ammonia / 1 h / -78 - -33 °C
5.1: 95 percent / 1 M HCl / tetrahydrofuran / 25 °C
6.1: 91 percent / diethyl ether / 1 h / 25 °C
7.1: 86 percent / AIBN / xylene / 18 h / 120 °C
8.1: POCl3 / hexamethylphosphoric acid triamide / 1 h / 25 °C
8.2: 81 percent / pyridine / hexamethylphosphoric acid triamide / 18 h / 150 °C
9.1: 84 percent / SnCl4 / CH2Cl2 / 20 h / -20 - 0 °C
10.1: NaBH4 / ethanol / 0.5 h
10.2: 74 percent / Raney Nickel / tetrahydrofuran / 0.17 h / 65 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 25 °C
12.1: 16.8 mg / MaHMDS / tetrahydrofuran / 18 h / 25 °C
13.1: 93 percent / LiBr / dimethylformamide / 3 h / 160 °C
With
hydrogenchloride; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tin(IV) chloride; lithium; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium bromide; tert-butyl alcohol; trichlorophosphate;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; ammonia; N,N-dimethyl-formamide; xylene; benzene;
9.1: Diels-Alder cycloaddition / 11.1: Dess-Martin oxidation / 12.1: Wittig olefination;
DOI:10.1021/jo0159035