Multi-step reaction with 8 steps
1.1: DIBAL-H / toluene / 1 h / -78 °C
1.2: 94 percent / benzene / 8 h / 20 °C
2.1: 95 percent / DIBAL-H / CH2Cl2; toluene / 0.17 h / -78 °C
3.1: 90 percent / Ti(Oi-Pr)4; (-)-diethyl-D-tartrate; TBHP / CH2Cl2; 2,2,4-trimethyl-pentane / 5 h / -20 °C
4.1: DMSO; Et3N; SO3*Py / CH2Cl2 / 2 h / 20 °C
4.2: 79 percent / benzene / 8 h / 20 °C
5.1: 82 percent / CSA / methanol / 0.08 h / 0 °C
6.1: 90 percent / Ph3P; Pd2(dba)3*CHCl3 / CH2Cl2 / 0.08 h / 20 °C
7.1: 86 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
8.1: hydrogen / Pd-C / ethanol / 2 h / 20 °C
With
2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; pyridine-SO3 complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
methanol; 2,2,4-trimethylpentane; ethanol; dichloromethane; toluene;
1.2: Wittig reaction / 3.1: Sharpless asymmetric epoxydation / 4.2: Wittig reaction;
DOI:10.3987/com-03-9952