Multi-step reaction with 33 steps
1.1: 29 percent / diacetoxyiodobenzene; iodine / CH2Cl2 / 0.83 h / 0 °C / Irradiation
2.1: 86 percent / i-Pr2NEt / CH2Cl2 / 10 h / 20 °C
3.1: O3 / CH2Cl2 / 0.25 h / -78 °C
3.2: 83 percent / PPh3 / CH2Cl2 / -78 - 20 °C
4.1: Zn(BH4)2 / diethyl ether / 0.5 h / 0 °C
5.1: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
6.1: 2.25 g / PPTS / acetone / 14 h / 20 °C
7.1: LiHMDS; HMPA / tetrahydrofuran / 1.5 h / -78 °C
7.2: 86 percent / tetrahydrofuran / 0.92 h / -78 - -40 °C
8.1: O3 / CH2Cl2 / 0.08 h / -78 °C
8.2: triphenylphosphine / CH2Cl2 / -78 - 20 °C
9.1: 197 mg / NaBH4 / CH2Cl2; methanol / 0.08 h / 20 °C
10.1: 97 percent / n-Bu3P / tetrahydrofuran / 1.67 h / -78 - 20 °C
11.1: 252 mg / H2O2 / tetrahydrofuran / 12 h / 20 °C
12.1: 335 mg / LiAlH4 / dioxane / 0.02 h / Heating
13.1: 345 mg / Et3N; DMAP / CH2Cl2 / 1.17 h / 20 °C
14.1: 93 percent / 4-methylmorpholine N-oxide / TPAP / acetonitrile / 1 h / 20 °C
15.1: O3 / CH2Cl2 / 0.67 h / -78 °C
15.2: 88 percent / triphenylphosphine / CH2Cl2 / -78 - 20 °C
16.1: 86 percent / SmI2; HMPA / tetrahydrofuran / 0.75 h / -40 - 0 °C
17.1: 87 percent / DMAP / tetrahydrofuran / 6 h / 20 °C
18.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.67 h / 20 °C
19.1: 98 percent / Dess-Martin periodinane / CH2Cl2 / 0.58 h / 20 °C
20.1: 90 percent / NaBH4; CeCl3*7H2O / methanol / 0.25 h / 0 °C
21.1: 77 percent / zinc chloride / CH2Cl2 / 0.75 h
22.1: 45 percent / (TMS)3SiH; AIBN / benzene / 0.33 h / Heating
23.1: 91 percent / cesium fluoride / dimethylformamide / 46 h / 130 °C
24.1: 91 percent / Dess-Martin periodinane / CH2Cl2 / 0.92 h / 20 °C
25.1: n-BuLi / tetrahydrofuran; hexane / 0.42 h / 20 °C
25.2: 92 percent / tetrahydrofuran; hexane / 0 - 20 °C
26.1: dicyclohexylborane / tetrahydrofuran / 0.33 h / 0 °C
26.2: 92 percent / H2O2; NaOH / tetrahydrofuran / 0 - 20 °C
27.1: 93 percent / i-Pr2NEt / CH2Cl2 / 0 - 20 °C
28.1: 98 percent / hydrogen / Pd(OH)2 on carbon / ethyl acetate / 0.5 h / 20 °C
29.1: 91 percent / Dess-Martin periodinane / CH2Cl2 / 1.08 h / 20 °C
30.1: tetrahydrofuran; hexane / 0 - 20 °C
30.2: 94 percent / t-BuOK / tetrahydrofuran / 1.08 h
31.1: 95 percent / hydrogen / Pd on carbon / ethyl acetate / 42 h / 20 °C
32.1: 88 percent / iodobenzene diacetate; iodine / CH2Cl2 / 1.75 h / 0 °C / Irradiation
33.1: 73 percent / DIBAL / CH2Cl2; hexane / 0.25 h / -78 °C
With
N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; samarium diiodide; cerium(III) chloride; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); tributylphosphine; [bis(acetoxy)iodo]benzene; tris-(trimethylsilyl)silane; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; zinc(II) chloride; lithium hexamethyldisilazane;
palladium on activated charcoal; tetrapropylammonium perruthennate; palladium hydroxide - carbon;
In
tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
11.1: Grieco olefination / 19.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation / 25.2: Wittig reaction / 29.1: Dess-Martin oxidation / 30.1: Wittig reaction;
DOI:10.1021/jo048681u