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Biomimetic and Biocatalytic Synthesis of Bruceol.

Aaron J DayJoel H Z LeeQuang D PhanHiu C LamAdam AmetovskiChristopher J SumbyStephen G BellJonathan H George
Published in: Angewandte Chemie (International ed. in English) (2018)
The first total synthesis of bruceol has been achieved using a biomimetic cascade cyclization initiated by a stereoselective Jacobsen-Katsuki epoxidation (and kinetic resolution) of racemic protobruceol-I. A bacterial cytochrome P450 monooxygenase was also found to catalyze the conversion of protobruceol-I into bruceol. The first full analysis of the NMR data of natural bruceol suggested that "isobruceol" was a previously unrecognized natural product also isolated from Philotheca brucei. This was confirmed by the re-isolation, synthesis, and X-ray analysis of isobruceol. In total, eight stereoisomers and structural isomers of bruceol have been synthesized in a highly divergent approach.
Keyphrases
  • high resolution
  • magnetic resonance
  • tissue engineering
  • solid state
  • machine learning
  • contrast enhanced