| The total synthesis of the originally proposed structure of briarellin J is reported in twenty-three linear steps from commercially available starting materials. Key reactions in the synthesis include an exo-selective Diels-Alder cycloaddition and a substrate-controlled stereoselective hydroboration. A revised structure of briarellin J is proposed based on evidence from the total synthesis, the proposed biosynthesis, and the original isolation data. The revised structure is proposed to be the C11 epimer of the originally proposed structure. Progress toward the synthesis of the revised structure is reported. |
