Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes

Abstract

The biocatalytic oxidative tandem decarboxylation of C 7 –C 18 dicarboxylic acids to terminal C 5 –C 16 dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11‐dodecadiene (0.49 g L –1 ). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C 6 –C 11 ω‐alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4‐pentadiene; scale‐up allowed the isolation of 1,15‐hexadecadiene and 1,11‐dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.