Multi-step reaction with 16 steps
1.1: 13 mg / 2,6-lutidine / CH2Cl2 / 2.5 h / -78 °C
2.1: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2 / 3 h
3.1: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C
4.1: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / 2.33 h / -78 - 20 °C
5.1: 99 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H2O / 20 h / 20 °C
6.1: 96 percent / DMAP / pyridine
7.1: 76 percent / diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C
8.1: 52 percent / titanium tetrachloride; i-Pr2NEt / CH2Cl2 / 0.75 h / -78 - -50 °C
9.1: 86 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
10.1: 2,3-dichloro-5,6-dicyanobenzoquinone; water / CH2Cl2 / 0.5 h / 20 °C
10.2: 2,3-dichloro-5,6-dicyanobenzoquinone / CH2Cl2 / 0.5 h / 20 °C
11.1: 20.5 mg / Dess-Martin periodinate / CH2Cl2; pyridine; H2O / 6 h / 20 °C
12.1: 54 percent / aq. hydrogen fluoride-pyridine / acetonitrile; CHCl3 / 10 h / 20 °C
13.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 7 h / 20 °C
14.1: 88 percent / CrCl2; lithium iodide / tetrahydrofuran / 5 h / 20 °C
15.1: 70 percent / PdCl2(MeCN)2; Ph3As; Ag2O / tetrahydrofuran; H2O / 2 h / 20 °C
16.1: 70 percent / HF; pyridine / acetonitrile; CH2Cl2 / 96 h
With
pyridine; 2,6-dimethylpyridine; chromium dichloride; dmap; dichloro bis(acetonitrile) palladium(II); lithium hydroxide; n-butyllithium; oxalyl dichloride; triphenyl-arsane; hydrogen fluoride; water; titanium tetrachloride; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(l) oxide; lithium iodide;
In
tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; chloroform; water; acetonitrile;
4.1: Swern oxidation / 7.1: Wadsworth-Emmons condensation;
DOI:10.1021/jo0104429