Multi-step reaction with 16 steps
1.1: 91 percent / O3; PPh3 / CH2Cl2 / 1.5 h / -78 °C
2.1: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C
3.1: 58 percent / AcOH; Ac2O / 38 h / 20 °C
4.1: 96 percent / NaH; Bu4NI / tetrahydrofuran / 0 - 20 °C
5.1: 90 percent / (+)-camphorsulfonic acid / methanol; H2O / 2.5 h / 65 °C
6.1: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr
7.1: LiNEt2; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C
8.1: DMAP / CH2Cl2 / 18 h / 20 °C
9.1: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C
10.1: 70 percent / aq. HClO4 / acetonitrile / 1.25 h / 55 °C
11.1: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH2Cl2 / 1 h / 0 - 20 °C
12.1: 81 percent / Et3SiH; TfOH / acetonitrile; CH2Cl2 / 1 h / -50 - -20 °C
13.1: 95 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H2O / CH2Cl2 / 3.5 h / 20 °C
14.1: 97 percent / K2CO3; H2O / methanol / 15 h / 20 °C
15.1: 92 percent / 2,6-lutidine / CH2Cl2 / 0.25 h / 20 °C
16.1: MeLi; TMSCl / diethyl ether / 1 h / 0 °C
16.2: 48.9 mg / sBuLi / diethyl ether; cyclohexane / 2 h / 0 - 20 °C
With
2,6-dimethylpyridine; triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N-iodo-succinimide; chloro-trimethyl-silane; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; water; methyllithium; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; ozone; acetic acid; (+)-10-camphorsulfonic acid; triphenylphosphine; N-tosylimidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; benzene;
DOI:10.1002/hlca.200390328