PubMed · 10104683
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1990. Dioxins made simple.. https://pubmed.ncbi.nlm.nih.gov/10104683/
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The stress-responsive genes expressed against the exogenous addition of dibenzo-p-dioxin from the lignin-degrading basidiomycete, Phanerochaete chrysosporium, were determined utilizing a differential display reverse transcription-PCR technique. Six cDNA fragments, exhibiting a high homology with various proteins from other microorganisms, were identified via a BLAST search; that is, NADH-ubiquinone oxidoreductase (NUO), ATP/ADP carrier, uric acid-xanthine permease, manganese superoxide dismutase, 3-hydroxybutyryl-coenzyme A dehydrogenase, and cytoskeletal protein. The expression of NUO was also up-regulated by catechol and trihydroxybenzene but not by dibenzofuran, suggesting that NUO expression was initiated by the formation of quinone products through the reaction of extracellular one-electron oxidizing enzymes with dibenzo-p-dioxin.
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6-Bromomethyl-4H-1,3-dioxin has been prepared in three steps from allyl iodide. A variety of enolates were then alkylated with this bromide. The resulting 6-alkyl-4H-1,3-dioxins were either subjected to further multistep transformations and/or heated to effect facile retrocycloaddition reactions. The resulting enones smoothly participated in novel endo-conjugate addition reactions with both carbon and nitrogen nucleophiles. For example, several bicyclo[4.3.1]decan-3,10-diones, the carbon framework of the CP compounds, were constructed using this novel annulation strategy. In another natural product study, a benzazocine related to the heterocyclic framework of the ring-opened tautomeric form of FR-900482 was also prepared using this methodology. Finally, a piperidin-4-one obtained from a 6-endo conjugate addition was converted to the naturally occurring (2S,4R)-4-hydroxypipecolic acid. Collectively, these examples document the synthetic equivalency of dioxin 1 with bromomethyl vinyl ketone and, moreover, delineate a strategy for accomplishing the sequential reactions with nucleophiles at the alpha' followed by the beta electrophilic sites.