Biomimetic and Biocatalytic Synthesis of Bruceol

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 catalyse the conversion of protobruceol‐I into bruceol. The first full analysis of the NMR data of natural bruceol suggested that "isobruceol" was a previously unrecognised natural product also isolated from Philotheca brucei. This was confirmed by the re‐isolation, synthesis and X‐ray analysis of isobruceol. In total, 8 stereoisomers and structural isomers of bruceol have been synthesized in a highly divergent approach.

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