Multi-step reaction with 13 steps
1.1: 86 percent / 3 h / 160 °C
2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C
3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C
3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C
4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C
5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C
5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C
6.1: pyridine / CH2Cl2 / 1 h / 0 °C
7.1: CH2Cl2 / 5 h / 20 °C
8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C
9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C
10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C
10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C
11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating
12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C
13.1: 30 percent / m-CPBA / CHCl3 / 5 h / -10 - 0 °C
With
pyridine; n-butyllithium; oxalyl dichloride; nitromethane; n-butanethiol; dimethylsulfide borane complex; (1R)-(+)-pinene; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; magnesium bromide; zinc;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; chloroform; water;
2.2: Wadsworth-Horner-Emmons reaction / 4.1: Swern oxidation / 10.2: Yamaguchi macrolactonization;
DOI:10.1021/jo048742o