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|Title:||Biomimetic and biocatalytic synthesis of bruceol|
|Citation:||Angewandte Chemie - International Edition, 2019; 58(5):1427-1431|
|Aaron J. Day, Joel H. Z. Lee, Quang D. Phan, Dr. Hiu C. Lam, Adam Ametovski, Christopher J. Sumby, Stephen G. Bell, Jonathan H. George|
|Abstract:||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.|
|Keywords:||biomimetic synthesis; biosynthesis; cascade reactions; natural products; total synthesis|
|Rights:||© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim|
|Appears in Collections:||Chemistry publications|
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