Multi-step reaction with 20 steps
1.1: 82 percent / Zn; NaI / methanol / 4 h / Heating
2.1: 85 percent / N-bromosuccinimide / CH2Cl2 / 1 h / 0 - 20 °C
3.1: 86 percent / (n-Bu)3SnH; AIBN / benzene / 0.5 h / Heating
4.1: 83 percent / CrO3; aq. H2SO4 / acetone / 1 h / 0 - 20 °C
5.1: 82 percent / triphenylphosphine / tetrahydrofuran / 3 h / Heating
6.1: 80 percent / Li sand / tetrahydrofuran / 2 h / Heating
7.1: 84 percent / imidazole / CH2Cl2 / 12 h / 0 - 20 °C
8.1: n-BuLi; BF3*OEt2 / tetrahydrofuran / -78 °C
8.2: 88 percent / tetrahydrofuran / -78 °C
9.1: 77 percent / LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 6 h / 155 °C
10.1: 82 percent / CSA / acetone / 1 h / 0 - 20 °C
11.1: 87 percent / Et3N; DMAP / CH2Cl2 / 12 h / 0 - 20 °C
12.1: 79 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C
13.1: 90 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 - 20 °C
14.1: 88 percent / methanol; CSA / CH2Cl2 / 0.5 h / 0 - 20 °C
15.1: 84 percent / IBX / dimethylsulfoxide; CH2Cl2 / 6 h / 0 - 20 °C
16.1: NaNH2 / diethyl ether / 6 h / 0 - 20 °C
16.2: 84 percent / diethyl ether / 0.33 h / 0 °C
17.1: 92 percent / imidazole / CH2Cl2 / 12 h / 0 - 20 °C
18.1: 84 percent / m-CPBA / CH2Cl2 / 6 h / 0 - 20 °C
19.1: n-BuLi; BF3*OEt3 / tetrahydrofuran / 0.17 h / -78 °C
19.2: 86 percent / tetrahydrofuran / 0.25 h / 0 °C
20.1: 86 percent / methanol; CSA / CH2Cl2 / 0.25 h / 0 °C
With
1H-imidazole; 2,6-dimethylpyridine; chromium(VI) oxide; methanol; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); methanesulfonamide; AD-mix-β; sulfuric acid; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; lithium; sodium amide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; zinc; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
camphor-10-sulfonic acid;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; diethylene glycol dimethyl ether; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;
4.1: Jones' oxidation / 16.2: Wittig reaction;
DOI:10.1016/j.tetlet.2007.05.021