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DOI: 10.1039/A808146H (Paper) Reference Section for: Chem. Commun., 1998, 2713-2714

A formal synthesis of both atropenantiomers of desertorin C

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Rekha V. Kyasnoor and Melvyn V. Sargent

Abstract

Asymmetric synthesis of both enantiomers of 1,1′-(2′,4-dihydroxy-6,6′-dimethoxy-2,4′-dimethylbiphenyl-3,3′-diyl)bisethanone allows the formal synthesis of both enantiomers of 4,4′,7,7′-tetramethoxy-5,5′-dimethyl-6,8′- bicoumarin (desertorin C).

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  10. CD spectra: Degradation product λ(MeOH)/nm 227 and 270 (Δε 7.7 and –6.5). Synthetic product λ(MeCN)/nm 196, 216, 231, 275, 296 and 340 (Δε 10.4, –231.8, 18.3, –9.0, 3.8 and 1.9). The racemic diketone was not resolved on HPLC nor was its 1H NMR spectrum resolved in the presence of (S)-1-(anthracen-9-yl)-2,2,2-trifluoroethanol.
  11. CD spectrum: λ(MeCN)/nm 196, 216, 230, 276, 295 and 335 (Δε–19.8, 52.7, –33.5, 14.7, –7.5 and –5.2).
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