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The absolute stereochemistry at the C 3 (and C 3', where appropriate) chiral centre(s) in the coupled dihydroanthracenones, the icterinoidins A1 and B1 and atrovirin B2 (from Dermocybe icterinoides), is deduced by application of the 'syn-anti rule', which relies on an empirical relationship between the sign of the Cotton effect couplet centred close to 275 nm in the CD spectrum and the chemical shift of the enantiotopic methylene protons at C 4 in the 1 H NMR spectrum of these pre-anthraquinones. The conclusions also allow assignment of central stereochemistry to atrovirin B1 (from Cortinarius atrovirens). In addition, we have applied Steglich's kinetic resolution method to confirm the (P)-axial configuration of icterinoidin B1, previously deduced by using Nakanishi's 'exiton chirality' method.

Absolute stereochemistry of fungal metabolites: icterinoidins A1 and B1, and atrovirins B1 and B2