Biomimetic Synthetic Studies on the Bruceol Family of Meroterpenoid Natural Products
A biomimetic approach to total synthesis can offer several benefits, including the development of cascade reactions for the rapid generation of molecular complexity, and guidance in the structure revision of old natural products and the anticipation of ne
Day, Aaron J.,George, Jonathan H.,Sumby, Christopher J.
(2020/02/04)
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 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.
Day, Aaron J.,Lee, Joel H. Z.,Phan, Quang D.,Lam, Hiu C.,Ametovski, Adam,Sumby, Christopher J.,Bell, Stephen G.,George, Jonathan H.
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p. 1427 - 1431
(2019/01/05)
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