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Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A
- Lan, Ping, White, Lauren E., Taher, Ehab S., Guest, Prudence E., Banwell, Martin G., Willis, Anthony
- Journal of natural products 2015 v.78 no.8 pp. 1963-1968
- enantiomers, nuclear magnetic resonance spectroscopy, spectral analysis, stereochemistry
- Total syntheses of (+)-asperpentyn (1) and compound ent-2, the enantiomer of the structure, 2, assigned to the natural product aspergillusol A are reported. Both reaction sequences employ the enzymatically derived and enantiomerically pure cis-1,2-dihydrocatechol 4 as starting material and use Sonogashira cross-coupling chemistry to install the required enyne side-chain. The ¹H and ¹³C NMR spectroscopic data derived from compound ent-2 match those reported for aspergillusol A, thus suggesting that the gross structure of this natural product has been assigned correctly, although its absolute stereochemistry remains unclear.