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Award ID contains: 1806581

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  1. ; ; ; (, Angewandte Chemie International Edition)
    Abstract Phenylfuropyridone natural products from fungi exhibit a range of antibacterial and cytotoxicity activities, and can potentiate azole antifungal compounds. We elucidated the biosynthetic pathway of compounds in the citridone family through heterologous reconstitution of thepfppathway. We demonstrate that multiple members of this family can be accessed from a reactiveortho‐quinone methide (o‐QM) intermediate through electrocyclization, cycloisomerization, or conjugate addition. Formation of the quaternary carbon center in citridone B is catalyzed by an epoxide‐forming P450 enzyme, followed by carbon skeletal rearrangement. Our results showcase how nature harvests the reactivities of ano‐QM intermediate to biosynthesize complex natural products. 
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  2. ; ; ; ; (, Angewandte Chemie International Edition)
    Abstract The combination of electrocyclizations and cycloadditions accounts for the formation of a range of fascinating natural products. Cascades consisting of 8π electrocyclizations followed by a 6π electrocyclization and a cycloaddition are relatively common. We now report the synthesis of the tetramic acid PF‐1018 through an 8π electrocyclization, the product of which is immediately intercepted by a Diels–Alder cycloaddition. The success of this pericyclic cascade was critically dependent on the substitution pattern of the starting polyene and could be rationalized through DFT calculations. The completion of the synthesis required the instalment of a trisubstituted double bond by radical deoxygenation. An unexpected side product formed through 4‐exo‐trig radical cyclization could be recycled through an unprecedented triflation/fragmentation. 
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  3. ; ; ; ; ; ; ; ; ; ; et al (, Nature)
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  4. ; ; ; ; ; ; ; ; (, Accounts of Chemical Research)
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  5. ; ; ; ; ; ; ; ; ; ; et al (, Journal of the American Chemical Society)
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  6. ; ; ; ; ; ; ; (, Nature Chemistry)
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  7. ; ; ; ; (, Natural Product Reports)
    Covering: 2000 to 2018 Pericyclic reactions are a distinct class of reactions that have wide synthetic utility. Before the recent discoveries described in this review, enzyme-catalyzed pericyclic reactions were not widely known to be involved in biosynthesis. This situation is changing rapidly. We define the scope of pericyclic reactions, give a historical account of their discoveries as biosynthetic reactions, and provide evidence that there are many enzymes in nature that catalyze pericyclic reactions. These enzymes, the “pericyclases,” are the subject of this review. 
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  8. ; ; ; ; ; ; (, Journal of the American Chemical Society)
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  9. ; ; ; ; ; (, Journal of the American Chemical Society)
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  10. ; ; ; ; ; (, Journal of the American Chemical Society)
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