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The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine‐2,3‐dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross‐coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary...
The possible involvement of 6π electrocyclic ring closures, mediated by electrocyclase enzymes, of polyunsaturated acyclic polyketide intermediates in the biosynthesis of certain o-dialkyl-substituted benzenoid natural products is discussed. The feasibility of the process is illustrated by the electrocyclic ring closure of 7E,9Z,11E,13Z-1-t-butyldimethylsilyloxy-hexadeca-7,9,11,13-tetraene (12a) to...
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