Multi-step reaction with 14 steps
1.1: 81 percent / Zn; NH4Cl / methanol / 6 h / 25 °C
2.1: 95 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 - 25 °C
3.1: 85 percent / LiBH4 / tetrahydrofuran; methanol / 3 h / -78 - 0 °C
4.1: 89 percent / NaHCO3; Dess-Martin periodinane / CH2Cl2; dimethylsulfoxide / 1.5 h / 25 °C
5.1: BF3*Et2O / tetrahydrofuran; hexane / 0.5 h / -78 °C
5.2: tetrahydrofuran; hexane / 3 h / -78 °C
5.3: 1.123 g / aq. H2O2; NaOH / methanol; tetrahydrofuran; hexane / 16 h / 0 - 25 °C
6.1: Ph3CBF4 / diethyl ether / 18 h / 25 °C
7.1: O3 / CH2Cl2 / -78 °C
7.2: PPh3 / CH2Cl2 / 1 h / -78 - 25 °C
8.1: 0.908 g / benzene / 16 h / 80 °C
9.1: 87 percent / DIBAL-H / toluene / 1 h / 0 °C
10.1: Et3N / tetrahydrofuran / 1 h / 0 °C
11.1: 2.888 g / LiBr / tetrahydrofuran / 0.5 h / 25 °C
12.1: LDA / tetrahydrofuran / 2.5 h / -78 °C
12.2: 91 percent / tetrahydrofuran / 1 h / -78 °C
13.1: LDA / tetrahydrofuran / 1 h / -78 °C
13.2: tetrahydrofuran / 1 h / -78 °C
14.1: 1.02 g / aq. (CO2H)2 / diethyl ether / 48 h / 25 °C
With
2,6-dimethylpyridine; lithium borohydride; boron trifluoride diethyl etherate; trityl tetrafluoroborate; oxalic acid; diisobutylaluminium hydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; ozone; triethylamine; lithium bromide; zinc; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; toluene; benzene;
5.2: Brown crotylboration / 8.1: Wittig olefination;
DOI:10.1039/b602020h