Chemoenzymatic Total Synthesis of (+)- & (−)-cis-Osmundalactone

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Abstract

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.

Details

Original languageEnglish
Pages (from-to)280-284
Number of pages5
JournalJOURNAL OF MOLECULAR CATALYSIS B: ENZYMATIC
Volume134
Publication statusPublished - 12 Nov 2016
MoE publication typeA1 Journal article-refereed

    Research areas

  • biocatalysis, natural products, peroxidase, DEHYDROGENASE, oxidative rearrangement, chemoenzymatic

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