title: Stereodivergent strategy for neurofuran synthesis via palladium-catalyzed asymmetric allylic cyclization: total synthesis of 7-epi-ST-Δ(8)-10-neurofuran.
abstract: Neurofurans are formed in vivo in the human brain as a consequence of an increased oxidative stress, and they could be valuable biomarkers of the neuronal oxidative stress. In this paper, an enantioselective stereodivergent approach to two key neurofuran precursors, belonging to the AC and ST classes, has been developed starting from a single achiral precursor, the meso-diol 11. The absolute configuration of the THF cores was secured by a Pd-catalyzed asymmetric allylic alkylation using (S,S)-L1 and (R,R)-L2 ligands, respectively.
authors: Department of Chemistry, University of Pavia, Viale Taramelli, 10-27100 Pavia, Italy.
authors: Matteo
authors: M
authors: Valli
authors: Paolo
authors: P
authors: Bruno
authors: Davide
authors: D
authors: Sbarbada
authors: Alessio
authors: A
authors: Porta
authors: Giovanni
authors: G
authors: Vidari
authors: Giuseppe
authors: G
authors: Zanoni
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C584629:7-epi-ST-delta(8)-10-neurofuran; D000498:Allyl Compounds; D005663:Furans; D010165:Palladium