Both optical antipodes of the cis-isomers of osmundalactone, a hydroxypyranone natural product and core structure of the angiopterlactones, have been synthesized from acetylfuran in only three steps through a redox cascade utilizing oxidoreductases and transition metal catalysis in a concerted fashion. The key step in this fully catalytic strategy is the enzyme-mediated Achmatowicz reaction via selective furan oxygenation to furnish the pyran core structure.
- natural products
- oxidative rearrangement
Blume, F., Liu, Y-C., Thiel, D., & Deska, J. (2016). Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone. JOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC, 134, 280-284. https://doi.org/10.1016/j.molcatb.2016.11.010