Synthesis of Racemic Tenellin

Article abstract of DOI:10.1021/jo00136a005

Total synthesis of racemic tenellin, a yellow pigment of the insect pathogenic fungus Beauveria, has been accomplished.Preparation of 1,4-dihydroxy-5-(p-hydroxyphenyl)-2(1H)-pyridinone is achieved in excellent overall yield by utilizing an intramolecular C-acylation of an imidazolide precursor.A facile conjugate reduction of the vinylogous amide 6 is illustrated with sodium cyanoborohydride.