Multi-step reaction with 8 steps
1: 1.) 0.59M LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 5.5 h
2: 1.) 1.65M BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, 1 h
3: 838 mg / 4N HCl / dioxane / Ambient temperature
4: oxalyl chloride / benzene / 2 h / 60 °C
5: pyridine / tetrahydrofuran / 1.5 h / -15 °C
6: H2 / 10percent Pd/C / methanol / 2 h / Ambient temperature
7: oxalyl chloride / benzene / 2 h / 50 °C
8: N-ethylmorpholine / tetrahydrofuran / 1.) -15 deg C to r.t., 2.) r.t., overnight
With
N-ethylmorpholine;; pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; hydrogen; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; 1,4-dioxane; methanol; benzene;
DOI:10.7164/antibiotics.47.1481