title: Total synthesis of hybocarpone, a cytotoxic naphthazarin derivative from the lichen Lecanora hybocarpa, and related compounds.
abstract: The concise synthesis of the lichen-derived antitumor agent hybocarpone (1) and its analogs is described. A new synthetic approach is based on the direct oxidative dimerization of the available naphthazarin precursors in the formation of the binaphtho[2,3-b; 2,3-d]furantetraone structure. It was shown that the first step to tetrahydrofuran features is the bridging hindered S*,S* and R*,S* carbon-carbon bonds of the molecules, setting the relative configurations of the 5aS*,6aS*,12aS*,12bS* and 5aS*,6aR*,12aR*,12bS* diastereomers.
authors: Sergey V
authors: SV
authors: Dragana
authors: Michael A
authors: MA
authors: Pushilin
authors: Valery P
authors: VP
authors: Glazunov
authors: Vladimir A
authors: VA
authors: Denisenko
authors: Victor Ph
authors: VP
authors: Anufriev
mesh_terms: D019281:Dimerization; D008011:Lichens / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D009285:Naphthoquinones; C512017:hybocarpone; C005503:naphthazarin