Multi-step reaction with 11 steps
1.1: imidazole / dimethylformamide
2.1: aq. Cp2ZrCl2 / CH2Cl2 / 4 h / -23 °C
2.2: I2 / tetrahydrofuran
3.1: Pd(PPh3)4 / tetrahydrofuran; dimethylformamide
4.1: TBAF / tetrahydrofuran
5.1: Dess-Martin periodinane / CH2Cl2
6.1: Sn(OTf)2; 1-ethylpiperidine / CH2Cl2
7.1: 2,6-lutidine / CH2Cl2
8.1: DIBAL-H / toluene
9.1: Sn(OTf)2; 1-ethylpiperidine / CH2Cl2
10.1: MeONHMe*HCl; AlMe3 / CH2Cl2
10.2: 4-DMAP; pyridine / CH2Cl2 / 72 h / 20 °C
11.1: DIBAL-H / tetrahydrofuran / -78 °C
With
1-ethyl-piperidine; 1H-imidazole; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; zirconocene dichloride; tetrabutyl ammonium fluoride; trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; diisobutylaluminium hydride; Dess-Martin periodane;
tetrakis(triphenylphosphine) palladium(0);
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
3.1: Negishi coupling;
DOI:10.1055/s-2006-926263