Multi-step reaction with 14 steps
1.1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.2: tetrahydrofuran; hexane / 2 h / -78 °C
1.3: 77 percent / tetrahydrofuran; hexane / 0.83 h / -78 - 0 °C
2.1: 75 percent / calcium carbonate; mercury(II) perchlorate trihydrate / tetrahydrofuran; H2O / 0.08 h / 0 °C
3.1: tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 96 h / -35 °C
4.1: p-toluenesulfonic acid monohydrate / acetone / 0.13 h / 20 °C
5.1: 2.0 g / perchloric acid / CH2Cl2; H2O / 36 h / 20 °C
6.1: 84 percent / imidazole; 4-dimethylaminopyridine / CH2Cl2 / 0.5 h / 0 °C
7.1: 97 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide; various solvent(s) / 4 h / 20 °C
8.1: 45 percent / selenium(IV) oxide; pyridine / dioxane / 1.75 h / 120 °C / microwave irradiation
9.1: triphenylphosphine; diethyl azodicarboxylate / benzene / 1.5 h / 20 °C
10.1: 0.186 g / tert-butyl alcohol; LiDBB / tetrahydrofuran / 0.5 h / -78 °C
11.1: 96 percent / sodium hydride; N-(2,4,6-triisopropylbenzenesulfonyl)imidazole / tetrahydrofuran; various solvent(s) / 0 - 20 °C
12.1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
12.2: 87 percent / tetrahydrofuran; hexane / 2 h / -78 - 0 °C
13.1: 98 percent / calcium carbonate; mercury(II) perchlorate trihydrate / tetrahydrofuran; H2O / 0.08 h / 0 °C
14.1: 71 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 36 h / -35 °C
With
pyridine; 1H-imidazole; dmap; n-butyllithium; selenium(IV) oxide; perchloric acid; mercury(II) perchlorate; lithium 4,4′-di(tert-butyl)biphenyl; potassium tert-butylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; calcium carbonate; tetramethylammonium triacetoxyborohydride; tert-butyl alcohol; diethylazodicarboxylate; 1-[(2,4,6-triisopropylphenyl)sulfonyl]-1H-imidazole;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
9.1: Mitsunobu alkylation / 11.1: Fraser-Reid epoxidation;
DOI:10.1021/ol071282b